IL104737A0 - Preparation of 2-chloro-5-methyl-pyridine - Google Patents
Preparation of 2-chloro-5-methyl-pyridineInfo
- Publication number
- IL104737A0 IL104737A0 IL104737A IL10473793A IL104737A0 IL 104737 A0 IL104737 A0 IL 104737A0 IL 104737 A IL104737 A IL 104737A IL 10473793 A IL10473793 A IL 10473793A IL 104737 A0 IL104737 A0 IL 104737A0
- Authority
- IL
- Israel
- Prior art keywords
- chloro
- methylpyridine
- formula
- preparation
- phosgene
- Prior art date
Links
- VXLYOURCUVQYLN-UHFFFAOYSA-N 2-chloro-5-methylpyridine Chemical compound CC1=CC=C(Cl)N=C1 VXLYOURCUVQYLN-UHFFFAOYSA-N 0.000 title abstract 3
- YGYAWVDWMABLBF-UHFFFAOYSA-N Phosgene Chemical compound ClC(Cl)=O YGYAWVDWMABLBF-UHFFFAOYSA-N 0.000 abstract 4
- DMGGLIWGZFZLIY-UHFFFAOYSA-N 3-methyl-1-oxidopyridin-1-ium Chemical compound CC1=CC=C[N+]([O-])=C1 DMGGLIWGZFZLIY-UHFFFAOYSA-N 0.000 abstract 2
- GETQZCLCWQTVFV-UHFFFAOYSA-N trimethylamine Chemical compound CN(C)C GETQZCLCWQTVFV-UHFFFAOYSA-N 0.000 abstract 2
- 239000003085 diluting agent Substances 0.000 abstract 1
- 239000003814 drug Substances 0.000 abstract 1
- 239000002917 insecticide Substances 0.000 abstract 1
- BVFNCILLDOYABM-UHFFFAOYSA-M trimethyl-(5-methylpyridin-2-yl)azanium;chloride Chemical compound [Cl-].CC1=CC=C([N+](C)(C)C)N=C1 BVFNCILLDOYABM-UHFFFAOYSA-M 0.000 abstract 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
- C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
- C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D213/60—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom 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
- C07D213/72—Nitrogen atoms
- C07D213/73—Unsubstituted amino or imino radicals
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
- C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
- C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D213/60—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom 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
- C07D213/61—Halogen atoms or nitro radicals
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Pyridine Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Abstract
A novel process is provided for the preparation of 2-chloro-5-methylpyridine of the formula (I) <IMAGE> from 3-methylpyridine-1-oxide, of the formula (II), <IMAGE> and phosgene (COCl2), which is characterised in that, in a first step, the 3-methylpyridine-1-oxide is reacted with trimethylamine and then with phosgene, if appropriate in the presence of a diluent, at temperatures between -30 DEG C and +50 DEG C, and the novel intermediate trimethyl(5-methylpyridin-2-yl)ammonium chloride of the formula (III) <IMAGE> which is formed in this process is isolated as a crude intermediate or, if desired, further purified, and, in a second step, this intermediate of the formula (III) is reacted with phosgene at temperatures between 50 DEG C and 150 DEG C. 2-Chloro-5-methylpyridine (I) is known as an intermediate for pharmaceuticals and insecticides.
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE4204920 | 1992-02-19 | ||
| DE4212595A DE4212595A1 (en) | 1992-02-19 | 1992-04-15 | METHOD FOR PRODUCING 2-CHLORINE-5-METHYL-PYRIDINE |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| IL104737A0 true IL104737A0 (en) | 1993-06-10 |
| IL104737A IL104737A (en) | 1997-02-18 |
Family
ID=25911972
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| IL10473793A IL104737A (en) | 1992-02-19 | 1993-02-16 | Process and intermediates for the preparation of 2-chloro-5-methyl-pyridine |
Country Status (11)
| Country | Link |
|---|---|
| EP (1) | EP0556683B1 (en) |
| JP (1) | JP3186886B2 (en) |
| CN (2) | CN1040431C (en) |
| AT (1) | ATE137221T1 (en) |
| BR (1) | BR9300596A (en) |
| DE (2) | DE4212595A1 (en) |
| DK (1) | DK0556683T3 (en) |
| ES (1) | ES2085661T3 (en) |
| HU (1) | HU209859B (en) |
| IL (1) | IL104737A (en) |
| MX (1) | MX9300555A (en) |
Families Citing this family (14)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5502194A (en) * | 1992-02-19 | 1996-03-26 | Bayer Aktiengesellschaft | Process for the preparation of 2-halogeno-pyridine derivatives |
| DE4311247A1 (en) * | 1993-04-06 | 1994-10-13 | Bayer Ag | Process for the preparation of 2-halogenopyridine derivatives |
| ATE200665T1 (en) * | 1995-09-08 | 2001-05-15 | Nippon Soda Co | METHOD FOR PRODUCING 3-(AMINOMETHYL)-6-CHLORPYRIDINES |
| CN101260076B (en) * | 2007-03-08 | 2012-04-11 | 南京红太阳生物化学有限责任公司 | Preparation method of 2-chloro-5-methylpyridine |
| EP2842944B1 (en) | 2010-04-06 | 2017-03-15 | Nippon Soda Co., Ltd. | Method for producing nitrogen-containing heterocyclic compound |
| WO2012073217A1 (en) * | 2010-12-02 | 2012-06-07 | Nerviano Medical Sciences S.R.L. | Process for the preparation of morpholinyl anthracycline derivatives |
| CN102219732B (en) * | 2011-04-22 | 2013-04-17 | 安徽国星生物化学有限公司 | Preparation method for 2-chlorine-5-methylpyridine compound |
| CN102977008A (en) * | 2012-11-08 | 2013-03-20 | 安徽国星生物化学有限公司 | Synthetic method of 2-chloro-5-methylpyridine |
| TW201605852A (en) * | 2013-09-26 | 2016-02-16 | 美國禮來大藥廠 | Novel compounds and use for preparation of tau imaging agents and tau imaging formulations |
| CN108467357B (en) * | 2018-05-28 | 2020-04-17 | 江苏扬农化工集团有限公司 | Method for preparing 2-chloro-5-methylpyridine |
| WO2022099692A1 (en) * | 2020-11-16 | 2022-05-19 | 单县欣润化工有限公司 | Method and system for synthesizing 2-chloro-5-trifluoromethyl pyridine |
| CN115010657B (en) * | 2022-07-18 | 2024-01-23 | 江苏瑞祥化工有限公司 | A kind of continuous flow method for preparing 2-chloro-5-methylpyridine |
| CN116354876A (en) * | 2023-03-31 | 2023-06-30 | 四川大学 | A kind of synthetic method of high-purity 2-chloro-5-picoline |
| CN116924359B (en) * | 2023-06-05 | 2025-09-19 | 广州天赐高新材料股份有限公司 | Preparation method of difluoro sulfonyl imide salt |
Family Cites Families (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE3800179A1 (en) | 1988-01-07 | 1989-07-20 | Bayer Ag | METHOD FOR PRODUCING 2-CHLORINE-5-METHYL-PYRIDINE |
| DE4020055A1 (en) * | 1990-01-18 | 1991-07-25 | Bayer Ag | METHOD FOR PRODUCING SUBSTITUTED 2-CHLORINE PYRIDINES |
| DE4020053A1 (en) * | 1990-01-31 | 1991-08-01 | Bayer Ag | METHOD FOR PRODUCING 2-CHLORINE-5-METHYL-PYRIDINE |
| DE4020052A1 (en) * | 1990-06-23 | 1992-01-02 | Bayer Ag | METHOD FOR PRODUCING 2-CHLORINE-5-METHYL-PYRIDINE |
-
1992
- 1992-04-15 DE DE4212595A patent/DE4212595A1/en not_active Withdrawn
-
1993
- 1993-02-02 MX MX9300555A patent/MX9300555A/en not_active IP Right Cessation
- 1993-02-08 DE DE59302304T patent/DE59302304D1/en not_active Expired - Fee Related
- 1993-02-08 DK DK93101948.3T patent/DK0556683T3/en active
- 1993-02-08 AT AT93101948T patent/ATE137221T1/en not_active IP Right Cessation
- 1993-02-08 ES ES93101948T patent/ES2085661T3/en not_active Expired - Lifetime
- 1993-02-08 EP EP93101948A patent/EP0556683B1/en not_active Expired - Lifetime
- 1993-02-12 JP JP04610793A patent/JP3186886B2/en not_active Expired - Fee Related
- 1993-02-16 IL IL10473793A patent/IL104737A/en not_active IP Right Cessation
- 1993-02-17 BR BR9300596A patent/BR9300596A/en not_active IP Right Cessation
- 1993-02-18 HU HU9300445A patent/HU209859B/en not_active IP Right Cessation
- 1993-02-19 CN CN93102168.5A patent/CN1040431C/en not_active Expired - Fee Related
-
1997
- 1997-09-05 CN CN97118269A patent/CN1083434C/en not_active Expired - Fee Related
Also Published As
| Publication number | Publication date |
|---|---|
| CN1040431C (en) | 1998-10-28 |
| BR9300596A (en) | 1993-08-24 |
| IL104737A (en) | 1997-02-18 |
| EP0556683A1 (en) | 1993-08-25 |
| JP3186886B2 (en) | 2001-07-11 |
| DK0556683T3 (en) | 1996-08-12 |
| ATE137221T1 (en) | 1996-05-15 |
| CN1186805A (en) | 1998-07-08 |
| HU9300445D0 (en) | 1993-05-28 |
| HK1009445A1 (en) | 1999-06-04 |
| MX9300555A (en) | 1993-09-01 |
| DE4212595A1 (en) | 1993-08-26 |
| CN1083434C (en) | 2002-04-24 |
| HU209859B (en) | 1994-11-28 |
| EP0556683B1 (en) | 1996-04-24 |
| HUT64028A (en) | 1993-11-29 |
| DE59302304D1 (en) | 1996-05-30 |
| ES2085661T3 (en) | 1996-06-01 |
| JPH07252226A (en) | 1995-10-03 |
| CN1075476A (en) | 1993-08-25 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| FF | Patent granted | ||
| KB | Patent renewed | ||
| KB | Patent renewed | ||
| KB | Patent renewed | ||
| KB | Patent renewed | ||
| MM9K | Patent not in force due to non-payment of renewal fees |