SU687070A1 - Method of obtaining 2-amino-4/5h/-ketopyrrols - Google Patents
Method of obtaining 2-amino-4/5h/-ketopyrrolsInfo
- Publication number
- SU687070A1 SU687070A1 SU772507208A SU2507208A SU687070A1 SU 687070 A1 SU687070 A1 SU 687070A1 SU 772507208 A SU772507208 A SU 772507208A SU 2507208 A SU2507208 A SU 2507208A SU 687070 A1 SU687070 A1 SU 687070A1
- Authority
- SU
- USSR - Soviet Union
- Prior art keywords
- amino
- ketopyrroles
- chj
- synthesis
- general formula
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims description 5
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 8
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims description 4
- 239000011541 reaction mixture Substances 0.000 claims description 2
- 230000015572 biosynthetic process Effects 0.000 claims 2
- 150000001875 compounds Chemical class 0.000 claims 2
- 238000003786 synthesis reaction Methods 0.000 claims 2
- KKBAIHATHFJMQD-UHFFFAOYSA-N 5-aminopyrrol-3-one Chemical class NC1=CC(=O)C=N1 KKBAIHATHFJMQD-UHFFFAOYSA-N 0.000 claims 1
- 229910052783 alkali metal Inorganic materials 0.000 claims 1
- 150000001340 alkali metals Chemical class 0.000 claims 1
- 238000009835 boiling Methods 0.000 claims 1
- VIXWGKYSYIBATJ-UHFFFAOYSA-N pyrrol-2-one Chemical class O=C1C=CC=N1 VIXWGKYSYIBATJ-UHFFFAOYSA-N 0.000 claims 1
- 239000002904 solvent Substances 0.000 claims 1
- 239000007858 starting material Substances 0.000 claims 1
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- UKVQBONVSSLJBB-UHFFFAOYSA-N 2-pyridin-2-ylacetonitrile Chemical compound N#CCC1=CC=CC=N1 UKVQBONVSSLJBB-UHFFFAOYSA-N 0.000 description 2
- 125000004105 2-pyridyl group Chemical group N1=C([*])C([H])=C([H])C([H])=C1[H] 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 2
- BWOVACANEIVHST-UHFFFAOYSA-N 2-(1h-benzimidazol-2-yl)acetonitrile Chemical compound C1=CC=C2NC(CC#N)=NC2=C1 BWOVACANEIVHST-UHFFFAOYSA-N 0.000 description 1
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 1
- DKGAVHZHDRPRBM-UHFFFAOYSA-N Tert-Butanol Chemical compound CC(C)(C)O DKGAVHZHDRPRBM-UHFFFAOYSA-N 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 125000004494 ethyl ester group Chemical group 0.000 description 1
- SZJUWKPNWWCOPG-UHFFFAOYSA-N methyl 2-anilinoacetate Chemical compound COC(=O)CNC1=CC=CC=C1 SZJUWKPNWWCOPG-UHFFFAOYSA-N 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- TVMXDCGIABBOFY-UHFFFAOYSA-N octane Chemical compound CCCCCCCC TVMXDCGIABBOFY-UHFFFAOYSA-N 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
Landscapes
- Pyridine Compounds (AREA)
Description
(54) СПОСОБ ПОЛУЧЕНИЯ 2-АМИНО-4(5Н)-КЕТОПИРРОЛОВ(54) METHOD OF OBTAINING 2-AMINO-4 (5H) -KETOPYRROLOV
такого как трет.бутанол или пиридин .such as tert.butanol or pyridine.
Пример 1. Смесь 0,1 моль 2-цианметилбензимидазола, 0,11 моль метилового эфира анилиноуксусной кислоты и 0,4 моль трет.-бутилата натри в 50 мл пиридина нагревают в течение 3 час. Охлаждают реакционную смесь, пиридин удал ют в вакууме. К охлажденному остатку приливают 600 мл воды, а через 1 час - 28 мл уксусной кислоты. Отфильтровывают образовавшийс осадок .Example 1. A mixture of 0.1 mol of 2-cyanmethylbenzimidazole, 0.11 mol of anilinoacetic acid methyl ester and 0.4 mol of sodium tert.-butylate in 50 ml of pyridine is heated for 3 hours. Cool the reaction mixture, pyridine is removed in vacuo. 600 ml of water are added to the cooled residue, and after 1 hour 28 ml of acetic acid are added. The precipitate formed is filtered off.
Выход: 88% 1-фенил-2-амино-3- {бенэимидазол-2-ил)-4(5Н)-кетопиррола , т.пл. 290С (из н-пропанола).Yield: 88% 1-phenyl-2-amino-3- {benimidazol-2-yl) -4 (5H) -ketopyrrole, mp. 290С (from n-propanol).
Пример 2.Example 2
Из 2-цианметилпиридина и этилового эфира «-анилинопропиновой киспоты получают 1-фенил-2-амино-3-(пиридин-2-ил )-5-метил-4(5Н)-кетопиррол .From 2-cyanmethylpyridine and ethyl ester "-anilinopropic acid, 1-phenyl-2-amino-3- (pyridin-2-yl) -5-methyl-4 (5H) -ketopyrrole is obtained.
Выход: 74%, т.пл. (из октана ) .Yield: 74%, mp. (from octane).
Найдено,%: 15,8. Вычислено,%: 15,85,Found,%: 15.8. Calculated,%: 15.85,
Пример 3,Example 3
Из 2-цианметилпиридина и метилового эфира а-(4-броманилино)-масл ной кислоты получают 1-(4-бром-феQ нил)-2-амино-3-(пиридин-2-ил)-5-этил-4- (5Н)-кетопиррол.From 2-cyanmethylpyridine and a- (4-bromoanilino) -butyric acid methyl ester, 1- (4-bromo-feq-nyl) -2-amino-3- (pyridin-2-yl) -5-ethyl-4- (5H) -ketopyrrole.
ВЫХОД -76%, т.пл. 199 С (из этанола ) .EXIT -76%, so pl. 199 With (from ethanol).
Найдено,,6; Вг 22,4;Found, 6; Br 22.4;
Су Н« BrNjO. Вычислено,% NSu N "BrNjO. Calculated% N
11,7; ВГ 22,3.11.7; VG 22.3.
Claims (1)
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| SU772507208A SU687070A1 (en) | 1977-07-15 | 1977-07-15 | Method of obtaining 2-amino-4/5h/-ketopyrrols |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| SU772507208A SU687070A1 (en) | 1977-07-15 | 1977-07-15 | Method of obtaining 2-amino-4/5h/-ketopyrrols |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| SU687070A1 true SU687070A1 (en) | 1979-09-25 |
Family
ID=20717873
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| SU772507208A SU687070A1 (en) | 1977-07-15 | 1977-07-15 | Method of obtaining 2-amino-4/5h/-ketopyrrols |
Country Status (1)
| Country | Link |
|---|---|
| SU (1) | SU687070A1 (en) |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4643762A (en) * | 1984-08-27 | 1987-02-17 | Chevron Research Company | Herbicidal 5-amino-3-oxo-4-(3-substituted-phenyl)-4-pyrroline and derivatives thereof |
| EP2776437A4 (en) * | 2011-11-07 | 2015-06-24 | Sunovion Pharmaceuticals Inc | OPIOID RECEPTOR MODULATORS AND METHODS OF USE |
-
1977
- 1977-07-15 SU SU772507208A patent/SU687070A1/en active
Cited By (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4643762A (en) * | 1984-08-27 | 1987-02-17 | Chevron Research Company | Herbicidal 5-amino-3-oxo-4-(3-substituted-phenyl)-4-pyrroline and derivatives thereof |
| EP2776437A4 (en) * | 2011-11-07 | 2015-06-24 | Sunovion Pharmaceuticals Inc | OPIOID RECEPTOR MODULATORS AND METHODS OF USE |
| US9580409B2 (en) | 2011-11-07 | 2017-02-28 | Sunovion Pharmaceuticals, Inc. | Modulators of opioid receptors and methods of use thereof |
| AU2012335980B2 (en) * | 2011-11-07 | 2017-08-17 | Sunovion Pharmaceuticals Inc. | Modulators of opioid receptors and methods of use thereof |
| AU2012335980C1 (en) * | 2011-11-07 | 2017-12-14 | Sunovion Pharmaceuticals Inc. | Modulators of opioid receptors and methods of use thereof |
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