GB1208569A - Process for the production of pyridines - Google Patents
Process for the production of pyridinesInfo
- Publication number
- GB1208569A GB1208569A GB57567A GB57567A GB1208569A GB 1208569 A GB1208569 A GB 1208569A GB 57567 A GB57567 A GB 57567A GB 57567 A GB57567 A GB 57567A GB 1208569 A GB1208569 A GB 1208569A
- Authority
- GB
- United Kingdom
- Prior art keywords
- pyridines
- pyridine
- alkyl
- cycloalkyl
- aldehyde
- 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
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
- C07D213/06—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 containing only hydrogen and carbon atoms in addition to the ring nitrogen atom
- C07D213/08—Preparation by ring-closure
-
- 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
- C07D213/06—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 containing only hydrogen and carbon atoms in addition to the ring nitrogen atom
- C07D213/08—Preparation by ring-closure
- C07D213/09—Preparation by ring-closure involving the use of ammonia, amines, amine salts, or nitriles
- C07D213/10—Preparation by ring-closure involving the use of ammonia, amines, amine salts, or nitriles from acetaldehyde or cyclic polymers thereof
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Pyridine Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Abstract
1,208,569. Pyridines. IMPERIAL CHEMICAL INDUSTRIES Ltd. 18 Dec., 1967 [4 Jan., 1967], No. 575/67. Heading C2C. Pyridine or an alkyl-, cycloalkyl- or hydropyridine is prepared by contacting an aldehyde RCH 2 .CHO, where R is hydrogen or a C 1-8 alkyl or cycloalkyl group, with an ammonium salt in a solution comprising a free acid R<SP>1</SP>COOH, where R<SP>1</SP> is a C 1-8 alkyl, cycloalkyl, or aryl group. A dialkyl or dicycloalkyl C 3-8 ketone or a second aldehyde of the formula R<SP>11</SP>CHO, where R<SP>11</SP> is hydrogen or a C 1-8 alkyl, cycloalkyl or aryl group, may also be present. The preferred ammonium salts are those derived from the acid R<SP>1</SP>COOH. To increase the yield of pyridines and alkyl pyridines, rather than hydrogenated pyridines, molecular oxygen may be present. It is preferred to operate in the presence of a catalyst which is a salt of a metal of variable valency, e.g. Mn, Cu, and Co. An additional solvent, e.g. ethyl acetate, dioxane, may be used. It is preferred to operate at 10- 200‹ C. Products obtained in the examples include 3,5-diethyl-2-propyl-pyridine, α-picoline, 2,3 - dihydro - 3,5 - diethyl - 2 - propyl - pyridine (which may disproportionate to 1,2,3,6-tetrahydro-pyridine), pyridine and vinyl pyridines. Some 2-ethyl-hexenal is obtained when the aldehyde is n-butyraldehyde.
Priority Applications (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
GB57567A GB1208569A (en) | 1967-01-04 | 1967-01-04 | Process for the production of pyridines |
DE19681695296 DE1695296A1 (en) | 1967-01-04 | 1968-01-03 | Process for the preparation of pyridines |
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
GB57567A GB1208569A (en) | 1967-01-04 | 1967-01-04 | Process for the production of pyridines |
Publications (1)
Publication Number | Publication Date |
---|---|
GB1208569A true GB1208569A (en) | 1970-10-14 |
Family
ID=9706805
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
GB57567A Expired GB1208569A (en) | 1967-01-04 | 1967-01-04 | Process for the production of pyridines |
Country Status (2)
Country | Link |
---|---|
DE (1) | DE1695296A1 (en) |
GB (1) | GB1208569A (en) |
Cited By (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
EP0040698A1 (en) * | 1980-05-23 | 1981-12-02 | Lonza Ag | Process for the preparation of 3-picoline |
EP0056496A1 (en) * | 1981-01-09 | 1982-07-28 | Lonza Ag | Method for the manufacture of 3-picoline |
CN115286567A (en) * | 2022-08-12 | 2022-11-04 | 镇江中智化学科技有限公司 | One-pot synthesis of 3-bromopyridine |
Families Citing this family (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
FI77025C (en) * | 1981-03-18 | 1989-01-10 | Lonza Ag | FOERFARANDE FOER FRAMSTAELLNING AV 3-PIKOLIN. |
CH656879A5 (en) * | 1981-07-09 | 1986-07-31 | Lonza Ag | METHOD FOR PRODUCING 3,5-DIALKYLPYRIDINE. |
CH660733A5 (en) * | 1981-09-29 | 1987-06-15 | Lonza Ag | METHOD FOR PRODUCING 3-PICOLIN. |
-
1967
- 1967-01-04 GB GB57567A patent/GB1208569A/en not_active Expired
-
1968
- 1968-01-03 DE DE19681695296 patent/DE1695296A1/en active Pending
Cited By (5)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
EP0040698A1 (en) * | 1980-05-23 | 1981-12-02 | Lonza Ag | Process for the preparation of 3-picoline |
US4337342A (en) * | 1980-05-23 | 1982-06-29 | Lonza Ltd. | Process for the preparation of 3-picoline |
EP0056496A1 (en) * | 1981-01-09 | 1982-07-28 | Lonza Ag | Method for the manufacture of 3-picoline |
CN115286567A (en) * | 2022-08-12 | 2022-11-04 | 镇江中智化学科技有限公司 | One-pot synthesis of 3-bromopyridine |
CN115286567B (en) * | 2022-08-12 | 2024-04-19 | 镇江中智化学科技有限公司 | One-pot synthesis of 3-bromopyridine |
Also Published As
Publication number | Publication date |
---|---|
DE1695296A1 (en) | 1972-02-24 |
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Legal Events
Date | Code | Title | Description |
---|---|---|---|
PS | Patent sealed | ||
PLNP | Patent lapsed through nonpayment of renewal fees |