CN111423354A - Synthesis method of 1H-3-pyrrolidone compound - Google Patents
Synthesis method of 1H-3-pyrrolidone compound Download PDFInfo
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- CN111423354A CN111423354A CN202010185915.XA CN202010185915A CN111423354A CN 111423354 A CN111423354 A CN 111423354A CN 202010185915 A CN202010185915 A CN 202010185915A CN 111423354 A CN111423354 A CN 111423354A
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- C07D—HETEROCYCLIC COMPOUNDS
- C07D207/00—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D207/02—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D207/30—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having two double bonds between ring members or between ring members and non-ring members
- C07D207/34—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having two double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
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- B01J31/00—Catalysts comprising hydrides, coordination complexes or organic compounds
- B01J31/16—Catalysts comprising hydrides, coordination complexes or organic compounds containing coordination complexes
- B01J31/18—Catalysts comprising hydrides, coordination complexes or organic compounds containing coordination complexes containing nitrogen, phosphorus, arsenic or antimony as complexing atoms, e.g. in pyridine ligands, or in resonance therewith, e.g. in isocyanide ligands C=N-R or as complexed central atoms
- B01J31/1805—Catalysts comprising hydrides, coordination complexes or organic compounds containing coordination complexes containing nitrogen, phosphorus, arsenic or antimony as complexing atoms, e.g. in pyridine ligands, or in resonance therewith, e.g. in isocyanide ligands C=N-R or as complexed central atoms the ligands containing nitrogen
- B01J31/181—Cyclic ligands, including e.g. non-condensed polycyclic ligands, comprising at least one complexing nitrogen atom as ring member, e.g. pyridine
- B01J31/1825—Ligands comprising condensed ring systems, e.g. acridine, carbazole
- B01J31/183—Ligands comprising condensed ring systems, e.g. acridine, carbazole with more than one complexing nitrogen atom, e.g. phenanthroline
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- B01J31/22—Organic complexes
- B01J31/2204—Organic complexes the ligands containing oxygen or sulfur as complexing atoms
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- B01J31/00—Catalysts comprising hydrides, coordination complexes or organic compounds
- B01J31/26—Catalysts comprising hydrides, coordination complexes or organic compounds containing in addition, inorganic metal compounds not provided for in groups B01J31/02 - B01J31/24
- B01J31/28—Catalysts comprising hydrides, coordination complexes or organic compounds containing in addition, inorganic metal compounds not provided for in groups B01J31/02 - B01J31/24 of the platinum group metals, iron group metals or copper
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- B01J31/00—Catalysts comprising hydrides, coordination complexes or organic compounds
- B01J31/26—Catalysts comprising hydrides, coordination complexes or organic compounds containing in addition, inorganic metal compounds not provided for in groups B01J31/02 - B01J31/24
- B01J31/28—Catalysts comprising hydrides, coordination complexes or organic compounds containing in addition, inorganic metal compounds not provided for in groups B01J31/02 - B01J31/24 of the platinum group metals, iron group metals or copper
- B01J31/30—Halides
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- B—PERFORMING OPERATIONS; TRANSPORTING
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- B01J2531/00—Additional information regarding catalytic systems classified in B01J31/00
- B01J2531/80—Complexes comprising metals of Group VIII as the central metal
- B01J2531/84—Metals of the iron group
- B01J2531/842—Iron
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Abstract
The invention provides a method for synthesizing 1H-3-pyrrolidone compounds, which comprises the steps of taking aliphatic primary amine and β -diketone compounds as raw materials, uniformly mixing the raw materials with an iron complex catalyst and a copper salt cocatalyst in an organic solvent, reacting for 8-12 hours at 40-110 ℃, and separating and purifying after the reaction is finished to obtain the 1H-3-pyrrolidone compounds.
Description
Technical Field
The invention relates to the technical field of organic chemical industry, in particular to a preparation method of fine chemicals 1H-3-pyrrolidone compounds, and specifically relates to a synthesis method of important organic chemical intermediates 1H-3-pyrrolidone compounds.
Background
The heterocyclic segment of the 1H-3-pyrrolidone compound is a structure which is common in natural products, medicaments and bioactive components, but the method for artificially synthesizing the structure is not a plurality of methods at present. Most of the existing methods have harsh conditions, or the reaction process is difficult to control due to factors such as heat release and the like, so that the industrial amplification is hindered. Therefore, it is practical to develop a fast, mild, green and efficient method for constructing the structural unit. According to literature, the compounds are synthesized by taking gamma-butyrolactone or maleic anhydride as a raw material and performing hydroamination, but the pyrrolidone synthesized by the methods is single in structure, and the cost is greatly increased if the pyrrolidone is further modified. According to early literature reports, the synthesis method of the 1H-3-pyrrolidone compound can be synthesized by acylation cyclization under the promotion of copper trifluoroacetate in trifluoroacetic acid solvent by using enamine ketone as a raw material, the reaction yield is about 85%, but the cost of a catalytic system is high, the industrialization is difficult to realize, the method for synthesizing the 1H-3-pyrrolidone compound is simple, the target product can be obtained by using acetylacetone and primary amine as raw materials under the catalysis of hydrogen peroxide, but the reaction rate is too high, the heat release is serious, the amplification is difficult to control, and the oxidation system generates more byproducts, so that the method is not suitable for large-scale industrial production.
Disclosure of Invention
Aiming at the defects of the prior art, the invention aims to provide a new synthetic method for preparing 1H-3-pyrrolidone compounds. The technical problem to be solved is to select a new catalytic system to control the production cost, improve the yield and be suitable for industrial scale-up production.
The invention takes β -diketone compound and aliphatic primary amine as raw materials, in organic solvent, and in the presence of catalyst, the target product is obtained by one-step condensation and ring closure.
The technical scheme of the invention is as follows:
a synthesis method of 1H-3-pyrrolidone compounds comprises the steps of taking aliphatic primary amine and β -diketone compounds shown in a formula (I) as raw materials, and obtaining compounds shown in a formula (II) (target products: 1H-3-pyrrolidone compounds) through synthesis reaction, separation and purification, wherein the synthesis reaction is to uniformly mix the aliphatic primary amine, β -diketone compounds, organic solvents, iron complex catalysts and copper salt cocatalyst, and react at the temperature of 40-110 ℃ for 8-12 hours;
in the formula (I) or formula (II), R1Is hydrogen, methyl, ethyl, propyl, butyl, isopropyl, benzyl, p-chlorobenzyl, p-methylbenzyl, octyl or p-methoxybenzyl; r2Is methyl, ethyl, propyl, isopropyl or phenyl.
Preferably, the amount of the material of the catalyst (the sum of the amounts of the materials of the iron complex catalyst and the copper salt co-catalyst) is 1-5% of the amount of the aliphatic primary amine material on a molar basis; the mass ratio of the copper salt cocatalyst to the iron complex catalyst is 0.3:1-0.5: 1; still further, the amount of material of the catalyst is 3% of the amount of the aliphatic primary amine material on a molar basis; the mass ratio of the copper salt of the cocatalyst to the iron complex of the catalyst was 1:2.
Preferably, the ratio of the amount of the substance of the aliphatic primary amine to the β -dione compound is 1: 2.0-2.4.
The iron complex catalyst is a complex formed by the reaction of an iron source and a ligand, preferably the iron source is iron acetate, iron chloride or iron nitrate, the ligand is 1, 10-phenanthroline, triphenylphosphine, L-proline, L-alanine or L-lysine, and further the iron complex catalyst is a complex formed by the reaction of iron chloride and 1, 10-phenanthroline.
Preferably, the copper salt cocatalyst is selected from one or more of cuprous iodide, cuprous chloride, cupric oxide, cupric nitrate, cupric hydroxide and cupric acetate; further, the copper salt co-catalyst is cuprous iodide.
Preferably, the organic solvent is selected from one of toluene, xylene, DMSO, DMF, tetrahydrofuran, and 1, 4-dioxane; further, the organic solvent is toluene.
Preferably, the synthesis reaction temperature is 90 ℃ (90 ℃ ± 2 ℃, 2 ℃ is an error).
The specific operation steps are as follows:
(1) β -diketone compound and aliphatic primary amine are added into organic solvent, iron complex catalyst and copper salt cocatalyst with proportion are added under stirring, and reaction is carried out for 8-12 hours at 40-110 ℃;
(2) after the reaction is finished, adding distilled water into the reaction solution, stirring uniformly, separating two phases, extracting the water phase for three times by using ethyl acetate, combining organic phases, and drying by using anhydrous sodium sulfate;
(3) filtering the extractive solution, distilling under reduced pressure to remove solvent, separating the residual viscous substance by column chromatography or adding appropriate solvent for recrystallization to obtain pure product 1H-3-pyrrolidone.
The method has the advantages that the purity of the product synthesized by the method is more than or equal to 99 percent after purification (determined by HP L C), the yield reaches 85 percent, and as the catalyst is easy to obtain and cheap, the production process is simple, the production process is mild and the emission is low, the process design can be directly carried out on the basis of laboratory work, and the large-scale production can be realized.
Drawings
FIG. 1 is a single crystal diffractogram of the synthetic product of example 1.
Detailed Description
Example 1
Acetylacetone (22.0g, 220mmol), benzylamine (10.7g, 100mmol), a complex formed by ferric chloride and 1, 10-phenanthroline (3.0mmol), cuprous iodide (1.5mmol) and toluene (100ml) are added into a 250ml round bottom flask, stirring is opened, temperature is raised, reaction is carried out for 8 hours at 105 ℃ (105 +/-2 ℃), a bottle mouth is kept open, temperature rising is stopped, then deionized water (100ml) is added, the two phases are separated, the water phase is extracted with ethyl acetate for three times, organic phases are combined, dried by anhydrous sodium sulfate, filtered, reduced pressure distillation is carried out, and a concentrate is subjected to chromatographic column separation (a chromatographic column filler is silica gel, the ratio of petroleum ether to ethyl acetate is 5:1 in terms of leaching) or recrystallization separation (a mixed solvent of acetone and ethyl acetate) to obtain 21.1g of colorless crystals, the yield is 85%, the purity of the product is more than or equal to 99% (determined by HP L C), and the product is N-benzyl-1H-2-hydroxy-4-acetyl-5-methyl-3-pyrrolidone, and the diffraction result of single crystal.
Example 2
Acetylacetone (22.0g, 220mmol), N-butylamine (7.4g, 100mmol), a complex of ferric nitrate and L-lysine (3.0mmol), cuprous iodide (1.5mmol) and toluene (100ml) are added to a 250ml round bottom flask, the flask is opened, stirred and heated, the reaction is carried out for 8 hours at 105 ℃ (105 ℃ +/-2 ℃), the flask is kept open, the heating is stopped, then 100ml of deionized water is added, the two phases are separated, the aqueous phase is extracted three times with ethyl acetate, the organic phases are combined, dried with anhydrous sodium sulfate, filtered, distilled under reduced pressure, the concentrate is separated by a chromatographic column (the filler of the chromatographic column is silica gel, the ratio of petroleum ether to ethyl acetate is 5:1 in terms of leaching) or recrystallized (the mixed solvent of acetone and ethyl acetate), 15.1g of colorless crystals are obtained, the yield is 67%, the product purity is not less than 99% (determined by HP L C), and the product is N-butyl-1H-2-hydroxy-4-acetyl-5-methyl-3-pyrrolidone.
Example 3
Acetylacetone (22.0g, 220mmol), N-butylamine (7.4g, 100mmol), a complex of ferric chloride and L-proline (3.0mmol), copper oxide (1.5mmol) and DMSO (100ml) are added to a 250ml round bottom flask, the mixture is stirred open and heated, and the reaction is carried out at 105 ℃ (105 ℃ +/-2 ℃) for 8 hours, while the flask is kept open, the heating is stopped, then 100ml of deionized water is added, the two phases are separated, the aqueous phase is extracted three times with ethyl acetate, the organic phases are combined, dried with anhydrous sodium sulfate, filtered, distilled under reduced pressure, and the concentrate is separated by a chromatographic column (the filler of the chromatographic column is silica gel, the ratio of petroleum ether to ethyl acetate is 5:1 in terms of leaching) or recrystallization separation (the mixed solvent of acetone and ethyl acetate) to obtain 15.1g of colorless crystals, the yield is 67%, the purity of the product is not less than 99% (determined by HP L C), and the product is N-butyl-1H-2-hydroxy-4-acetyl-5 methyl-3-pyrrolidone.
Example 4
Adding benzoylacetone (35.6g, 220mmol), N-propylamine (5.9g, 100mmol), a complex formed by ferric chloride and 1, 10-phenanthroline (3.0mmol), cuprous iodide (1.5mmol) and toluene (100ml) into a 250ml round bottom flask, stirring and heating up, reacting for 8 hours at 105 ℃ (105 ℃ +/-2 ℃), stopping heating, adding deionized water (100ml), separating two phases, extracting the aqueous phase with ethyl acetate for three times, combining organic phases, drying with anhydrous sodium sulfate, filtering, distilling under reduced pressure, separating the concentrate by a chromatographic column (the filler of the chromatographic column is silica gel, the ratio of petroleum ether to ethyl acetate is 5:1) or separating by recrystallization (the mixed solvent of acetone and ethyl acetate), obtaining 19.2g of colorless crystals, the yield is 71%, the purity is more than or equal to 99% (measured by HP L C), and the product is N-propyl-1H-2-hydroxy-4-benzoyl-5-methyl-3-pyrrolidone.
Example 5
Acetylacetone (22.0g, 220mmol), p-chlorobenzylamine (14.1g, 100mmol), a complex (3.0mmol) formed by ferric sulfate and 1, 10-phenanthroline, cuprous iodide (1.5mmol) and xylene (100ml) are added into a 250ml round bottom flask, stirring is opened, heating is carried out, reaction is carried out for 8 hours at 105 ℃ (105 +/-2 ℃), a bottle mouth is kept open, heating is stopped, then deionized water (100ml) is added, the two phases are separated, the water phase is extracted for three times by ethyl acetate, the organic phase is combined, dried by anhydrous sodium sulfate, filtered, distilled under reduced pressure, and the concentrate is separated by a chromatographic column (the filler of the chromatographic column is silica gel, the ratio of petroleum ether to ethyl acetate is 5:1) or recrystallized and separated (the mixed solvent of acetone and ethyl acetate), so that 23.1g of colorless crystals are obtained, the yield is 79%, the purity of the product is more than or equal to 99% (measured by HP L C), and the product is N-p-chlorobenzyl-1H-2-hydroxy-4-acetyl-5-methyl-3.
Example 6
Acetylacetone (22.0g, 220mmol), octylamine (7.3g, 100mmol), a complex (4.0mmol) formed by ferric nitrate and 1, 10-phenanthroline, cuprous iodide (2.0mmol) and toluene (100ml) are added into a 250ml round bottom flask, stirring is started, temperature is raised, reaction is carried out for 8 hours at 110 ℃ (110 +/-2 ℃), a bottle mouth is kept open, temperature rising is stopped, then deionized water (100ml) is added, the two phases are separated, the water phase is extracted for three times by ethyl acetate, the organic phase is combined, dried by anhydrous sodium sulfate, filtered, distilled under reduced pressure, and the concentrate is separated by a chromatographic column (the filler of the chromatographic column is silica gel, the ratio of petroleum ether to ethyl acetate is 5:1) or recrystallization separation is carried out (the mixed solvent of acetone and ethyl acetate), colorless crystals (19.0 g, the yield is 83%, the product purity is more than or equal to 99% (measured by HP L C) are obtained, and the product is N-octyl-1H-2-hydroxy-4-acetyl-5 methyl-3-pyrrolidone.
Example 7
Acetylacetone (22.0g, 220mmol), octylamine (7.3g, 100mmol), a complex (4.0mmol) formed by ferric nitrate and 1, 10-phenanthroline, cuprous iodide (2.0mmol) and toluene (100ml) are added into a 250ml round bottom flask, stirring is started, temperature is raised, reaction is carried out for 8 hours at 40 ℃ (40 ℃ +/-2 ℃), a bottle mouth is kept open, temperature rising is stopped, then deionized water (100ml) is added, the two phases are separated, the water phase is extracted for three times by ethyl acetate, the organic phase is combined, dried by anhydrous sodium sulfate, filtered, distilled under reduced pressure, and the concentrate is separated by a chromatographic column (the filler of the chromatographic column is silica gel, the ratio of petroleum ether to ethyl acetate is 5:1 according to leaching meter) or separated by recrystallization (the mixed solvent of acetone and ethyl acetate), so as to obtain 5.7g of colorless crystals, the yield is 25%, the purity of the product is more than or equal to 99% (measured by HP L C), and the product is N-octyl-1H-2-hydroxy-4-acetyl-.
Example 8
Acetylacetone (22.0g, 220mmol), octylamine (7.3g, 100mmol), a complex (5.0mmol) formed by ferric nitrate and 1, 10-phenanthroline, cuprous iodide (3.0mmol) and toluene (100ml) are added into a 250ml round bottom flask, stirring is started, temperature is raised, reaction is carried out for 12 hours at 40 ℃ (40 ℃ +/-2 ℃), a bottle mouth is kept open, heating is stopped, then deionized water (100ml) is added, the two phases are separated, the water phase is extracted for three times by ethyl acetate, the organic phase is combined, dried by anhydrous sodium sulfate, filtered, distilled under reduced pressure, and the concentrate is separated by a chromatographic column (the filler of the chromatographic column is silica gel, the ratio of petroleum ether to ethyl acetate is 5:1) or recrystallization separation is carried out (the mixed solvent of acetone and ethyl acetate), so that 7.9g of colorless crystals is obtained, the yield is 35%, the purity of the product is more than or equal to 99% (measured by HP L C), and the product is N-octyl-1H-2-hydroxy-4-acetyl-5 methyl-.
Example 9
Acetylacetone (22.0g, 220mmol), octylamine (7.3g, 100mmol), a complex (4.0mmol) formed by ferric nitrate and 1, 10-phenanthroline, cuprous iodide (1.2mmol) and toluene (100ml) are added into a 250ml round bottom flask, stirring is opened, temperature is raised, reaction is carried out for 8 hours at 110 ℃ (110 ℃ +/-2 ℃), a bottle mouth is kept open, heating is stopped, then deionized water (100ml) is added, the two phases are separated, the water phase is extracted for three times by ethyl acetate, the organic phase is combined, dried by anhydrous sodium sulfate, filtered, distilled under reduced pressure, and the concentrate is separated by a chromatographic column (the filler of the chromatographic column is silica gel, the ratio of petroleum ether to ethyl acetate is 5:1) or recrystallization separation is carried out (the mixed solvent of acetone and ethyl acetate), so that 14.5.0g of colorless crystals is obtained, the yield is 63.4%, the purity of the product is more than or equal to 99% (measured by HP L C), and the product is N-octyl-1H-2-hydroxy-4-acetyl-5 methyl-.
Example 10
Acetylacetone (22.0g, 220mmol), octylamine (7.3g, 100mmol), a complex (1.0mmol) formed by ferric nitrate and 1, 10-phenanthroline, cuprous iodide (0.5mmol) and toluene (100ml) are added into a 250ml round bottom flask, stirring is started, temperature is raised, reaction is carried out for 8 hours at 110 ℃ (110 ℃ +/-2 ℃), a bottle mouth is kept open, temperature rising is stopped, then deionized water (100ml) is added, the two phases are separated, the water phase is extracted for three times by ethyl acetate, the organic phase is combined, dried by anhydrous sodium sulfate, filtered, distilled under reduced pressure, and the concentrate is separated by a chromatographic column (the filler of the chromatographic column is silica gel, the ratio of petroleum ether to ethyl acetate is 5:1) or recrystallization separation is carried out (the mixed solvent of acetone and ethyl acetate), so that 9.5.0g of colorless crystals is obtained, the yield is 41.5%, the purity of the product is more than or equal to 99% (measured by HP L C), and the product is N-octyl-1H-2-hydroxy-4-acetyl-5 methyl.
Example 11
Acetylacetone (22.0g, 220mmol), octylamine (7.3g, 100mmol), a complex (4.0mmol) formed by ferric nitrate and 1, 10-phenanthroline, cuprous iodide (2.0mmol) and toluene (100ml) are added into a 250ml round bottom flask, stirring is started, temperature is raised, reaction is carried out for 8 hours at 90 ℃ (90 ℃ +/-2 ℃), a bottle mouth is kept open, temperature rising is stopped, then deionized water (100ml) is added, the two phases are separated, the water phase is extracted for three times by ethyl acetate, the organic phase is combined, dried by anhydrous sodium sulfate, filtered, distilled under reduced pressure, and the concentrate is separated by a chromatographic column (the filler of the chromatographic column is silica gel, the ratio of petroleum ether to ethyl acetate is 5:1) or recrystallization separation is carried out (the mixed solvent of acetone and ethyl acetate), colorless crystals (19.0 g, the yield is 83%, the purity of the product is more than or equal to 99% (measured by HP L C) are obtained, and the product is N-octyl-1H-2-hydroxy-4-acetyl-5 methyl-.
Comparative example 1
Acetylacetone (22.0g, 220mmol) and benzylamine (10.7g, 100mmol) are added into a 250ml round bottom flask, stirring is started, the temperature is increased, 24.9g of 30% hydrogen peroxide is dripped at 40 ℃, the reaction is carried out for 12 hours, a bottle mouth is kept open, the temperature is stopped increasing, then 100ml of deionized water is added, after two phases are separated, an aqueous phase is extracted with ethyl acetate for three times, an organic phase is combined, dried by anhydrous sodium sulfate, filtered and distilled under reduced pressure, and a concentrate is subjected to chromatographic column separation (a chromatographic column filler is silica gel, the ratio of petroleum ether to ethyl acetate is 5:1) or recrystallization separation (a mixed solvent of acetone and ethyl acetate) to obtain 16.1g of colorless crystals, the yield is 65%, the product purity is larger than or equal to 90% (measured by HP L C), and the product N-benzyl-1H-2-hydroxy-4-acetyl-5 methyl-3-pyrrolidone has more byproducts.
Claims (8)
1. A synthetic method of 1H-3-pyrrolidone compounds is characterized in that aliphatic primary amine shown in a formula (I) and β -diketone compounds are used as raw materials, and the compounds shown in a formula (II) are obtained after synthesis reaction, separation and purification, and the synthetic method is characterized in that the aliphatic primary amine, β -diketone compounds, organic solvents, iron complex catalysts and copper salt cocatalyst are uniformly mixed and react for 8-12 hours at the temperature of 40-110 ℃;
in the formula (I) or formula (II), R1Is hydrogen, methyl, ethyl, propyl, butyl, isopropyl, benzyl, p-chlorobenzyl, p-methylbenzyl, octyl or p-methoxybenzyl; r2Is methyl, ethyl, propyl, isopropyl or phenyl.
2. The method for synthesizing 1H-3-pyrrolidone compounds as claimed in claim 1, wherein: the amount of the catalyst material accounts for 1-5% of the amount of the aliphatic primary amine material; the mass ratio of the copper salt cocatalyst to the iron complex catalyst is 0.3:1-0.5: 1.
3. The method for synthesizing 1H-3-pyrrolidones compounds according to claim 2, wherein: the amount of the substance of the catalyst is 3% of the amount of the aliphatic primary amine substance; the mass ratio of the copper salt of the cocatalyst to the iron complex of the catalyst was 1:2.
4. The method for synthesizing 1H-3-pyrrolidone compounds as claimed in any one of claims 1 to 3, wherein the ratio of the amount of said aliphatic primary amine to the amount of said β -dione compound is 1: 2.0-2.4.
5. The method for synthesizing the 1H-3-pyrrolidone compound according to claim 1, wherein the iron complex catalyst is a complex formed by the reaction of an iron source and a ligand, the iron source is iron acetate, iron chloride or iron nitrate, and the ligand is 1, 10-phenanthroline, triphenylphosphine, L-proline, L-alanine or L-lysine.
6. The method for synthesizing 1H-3-pyrrolidone compounds as claimed in claim 1, wherein: the copper salt cocatalyst is one or more of cuprous iodide, cuprous chloride, copper oxide, copper nitrate, copper hydroxide and copper acetate.
7. The method for synthesizing 1H-3-pyrrolidone compounds as claimed in claim 1, wherein: the organic solvent is toluene, xylene, DMSO, DMF, tetrahydrofuran or 1, 4-dioxane.
8. The method for synthesizing 1H-3-pyrrolidone compounds as claimed in claim 1, wherein: the synthesis reaction temperature is 90 ℃.
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