GB789296A - Processes for producing coumarin derivatives - Google Patents
Processes for producing coumarin derivativesInfo
- Publication number
- GB789296A GB789296A GB21426/54A GB2142654A GB789296A GB 789296 A GB789296 A GB 789296A GB 21426/54 A GB21426/54 A GB 21426/54A GB 2142654 A GB2142654 A GB 2142654A GB 789296 A GB789296 A GB 789296A
- Authority
- GB
- United Kingdom
- Prior art keywords
- hydroxycoumarin
- give
- acetophenone
- aliphatic
- cyclohexanone
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired
Links
- 150000001893 coumarin derivatives Chemical class 0.000 title 1
- VXIXUWQIVKSKSA-UHFFFAOYSA-N 4-hydroxycoumarin Chemical group C1=CC=CC2=C1OC(=O)C=C2O VXIXUWQIVKSKSA-UHFFFAOYSA-N 0.000 abstract 4
- KWOLFJPFCHCOCG-UHFFFAOYSA-N Acetophenone Chemical compound CC(=O)C1=CC=CC=C1 KWOLFJPFCHCOCG-UHFFFAOYSA-N 0.000 abstract 4
- JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 abstract 4
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 abstract 3
- JECYUBVRTQDVAT-UHFFFAOYSA-N 2-acetylphenol Chemical compound CC(=O)C1=CC=CC=C1O JECYUBVRTQDVAT-UHFFFAOYSA-N 0.000 abstract 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 abstract 2
- 125000001931 aliphatic group Chemical group 0.000 abstract 2
- 229910052799 carbon Inorganic materials 0.000 abstract 2
- 150000002576 ketones Chemical class 0.000 abstract 2
- QXGVMMYCQMXNBK-UHFFFAOYSA-N 3-[(dimethylamino)methyl]-4-hydroxychromen-2-one Chemical compound C1=CC=C2OC(=O)C(CN(C)C)=C(O)C2=C1 QXGVMMYCQMXNBK-UHFFFAOYSA-N 0.000 abstract 1
- BLVHWCKQUXHPBC-UHFFFAOYSA-N 4-hydroxy-3-(3-oxo-3-phenylpropyl)chromen-2-one Chemical compound O=C1OC=2C=CC=CC=2C(O)=C1CCC(=O)C1=CC=CC=C1 BLVHWCKQUXHPBC-UHFFFAOYSA-N 0.000 abstract 1
- QHDYEKODQFJTCB-UHFFFAOYSA-N 4-hydroxy-3-[3-(2-hydroxyphenyl)-3-oxopropyl]chromen-2-one Chemical compound OC1=C(C(=O)CCC=2C(OC3=CC=CC=C3C2O)=O)C=CC=C1 QHDYEKODQFJTCB-UHFFFAOYSA-N 0.000 abstract 1
- -1 N,N-disubstituted 3-aminomethyl-4-hydroxycoumarin Chemical class 0.000 abstract 1
- 229930192627 Naphthoquinone Natural products 0.000 abstract 1
- 125000002723 alicyclic group Chemical group 0.000 abstract 1
- 150000001412 amines Chemical class 0.000 abstract 1
- 150000008365 aromatic ketones Chemical class 0.000 abstract 1
- 150000001721 carbon Chemical group 0.000 abstract 1
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 abstract 1
- OTAFHZMPRISVEM-UHFFFAOYSA-N chromone Chemical compound C1=CC=C2C(=O)C=COC2=C1 OTAFHZMPRISVEM-UHFFFAOYSA-N 0.000 abstract 1
- 150000004777 chromones Chemical class 0.000 abstract 1
- 125000002147 dimethylamino group Chemical group [H]C([H])([H])N(*)C([H])([H])[H] 0.000 abstract 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 abstract 1
- 239000000203 mixture Substances 0.000 abstract 1
- 150000002791 naphthoquinones Chemical class 0.000 abstract 1
- 229910052757 nitrogen Inorganic materials 0.000 abstract 1
- 230000020477 pH reduction Effects 0.000 abstract 1
- 125000000587 piperidin-1-yl group Chemical group [H]C1([H])N(*)C([H])([H])C([H])([H])C([H])([H])C1([H])[H] 0.000 abstract 1
- KRIOVPPHQSLHCZ-UHFFFAOYSA-N propiophenone Chemical compound CCC(=O)C1=CC=CC=C1 KRIOVPPHQSLHCZ-UHFFFAOYSA-N 0.000 abstract 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D311/00—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only hetero atom, condensed with other rings
- C07D311/02—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only hetero atom, condensed with other rings ortho- or peri-condensed with carbocyclic rings or ring systems
- C07D311/04—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring
- C07D311/42—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring with oxygen or sulfur atoms in positions 2 and 4
- C07D311/44—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring with oxygen or sulfur atoms in positions 2 and 4 with one hydrogen atom in position 3
- C07D311/46—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring with oxygen or sulfur atoms in positions 2 and 4 with one hydrogen atom in position 3 unsubstituted in the carbocyclic ring
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Pyrane Compounds (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Abstract
4-Hydroxycoumarins substituted in position 3 are prepared by reacting an N,N-disubstituted 3-aminomethyl-4-hydroxycoumarin of formula: <FORM:0789296/IV (b)/1> (where R is an aliphatic or cyclic amine residue, e.g. dimethylamino or piperidino) at an elevated temperature with a ketone having at least one hydrogen atom on the carbon atom in the a -position to the carbonyl group. The nitrogen is eliminated as an amine RH, thus obtaining a 4-hydroxycoumarin in which the 3-methyl residue is attached to the a -carbon of the ketone employed. Aliphatic, alicyclic or aromatic ketones may be used, particularly cyclohexanone, a -decalone, a -tetralone, acetophenone, p-halogeno-acetophenones, propiophenone, chalkones, chromones, and naphthoquinones. The reaction is normally complete in 10-15 minutes at about 165 DEG C. In examples: (1) 3-dimethylaminomethyl-4-hydroxycoumarin is heated with o-hydroxyacetophenone, mixture poured into 5 per cent NaOH, acidification yielding 3 - (o - hydroxybenzoylethyl) - 4 - hydroxycoumarin; (2) to (4) as in (1), using acetophenone to give 3-benzoylethyl-4-hydroxycoumarin; cyclohexanone to give 3-(21-oxo-cyclohexylmethyl) - 4 - hydroxycoumarin; and chromone to give 3-(chromonyl-31-methyl)-4-hydroxycoumarin respectively.
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CS325666X | 1953-07-23 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB789296A true GB789296A (en) | 1958-01-15 |
Family
ID=5452203
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB21426/54A Expired GB789296A (en) | 1953-07-23 | 1954-07-22 | Processes for producing coumarin derivatives |
Country Status (5)
| Country | Link |
|---|---|
| BE (1) | BE530546A (en) |
| CH (1) | CH325666A (en) |
| DE (1) | DE1081023B (en) |
| GB (1) | GB789296A (en) |
| NL (2) | NL93599C (en) |
Family Cites Families (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CH236350A (en) * | 1942-09-14 | 1945-01-31 | Hoffmann La Roche | Method for preparing a coumarin derivative. |
| US2427578A (en) * | 1945-04-02 | 1947-09-16 | Wisconsin Alumni Res Found | 3-substituted 4-hydroxycoumarin and process of making it |
-
0
- BE BE530546D patent/BE530546A/xx unknown
- NL NLAANVRAGE8005913,A patent/NL189446B/en unknown
- NL NL93599D patent/NL93599C/xx active
-
1954
- 1954-07-10 DE DES39952A patent/DE1081023B/en active Pending
- 1954-07-13 CH CH325666D patent/CH325666A/en unknown
- 1954-07-22 GB GB21426/54A patent/GB789296A/en not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| BE530546A (en) | |
| NL189446B (en) | |
| DE1081023B (en) | 1960-05-05 |
| NL93599C (en) | |
| CH325666A (en) | 1957-11-15 |
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