GB563171A - Manufacture of pyridine-3-acetic acid esters and quaternary compounds thereof - Google Patents
Manufacture of pyridine-3-acetic acid esters and quaternary compounds thereofInfo
- Publication number
- GB563171A GB563171A GB11226/42A GB1122642A GB563171A GB 563171 A GB563171 A GB 563171A GB 11226/42 A GB11226/42 A GB 11226/42A GB 1122642 A GB1122642 A GB 1122642A GB 563171 A GB563171 A GB 563171A
- Authority
- GB
- United Kingdom
- Prior art keywords
- pyridine
- acetic acid
- acid
- alcohol
- methyl ester
- 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
- C07D213/24—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 substituted hydrocarbon radicals attached to ring carbon atoms
- C07D213/54—Radicals substituted by carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
- C07D213/55—Acids; Esters
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Pyridine Compounds (AREA)
Abstract
Esters of pyridine-3-acetic acid are prepared by acting on pyridine 3-acetic acid or certain of its derivatives with an alcohol. Derivatives of the acid which may be used include the nitrile, amide, anhydride, halides and salts. Alcohols mentioned include saturated or unsaturated aliphatic, aliphatic - aromatic, or isocyclic alcohols, such as methanol, ethanol, propanol, isopropanol, amyl alcohol, benzyl alcohol, phenol, cyclohexanol, furyl carbinol and basic substituted alcohols such as diethylaminoethanol. Instead of the alcohols themselves, certain of their derivatives may be used, such as alcoholates, esters and ethers including alkyl halides, dialkyl sulphates, and diazoalkenes such as diazomethane. The esterification preferably takes place in the presence of a solvent which may either be an excess of the alcohol used in the esterification or an inert solvent such as benzene. Condensing agents such as hydrochloric, or sulphuric acid, phosphorus oxychloride, phosgene, an alkali or an alkaline earth carbonate, an alkali acetate, an alkaline earth halide, or a tertiary base such as pyridine. The quaternary derivatives of esters of pyridine-3-acetic acid may be either obtained from the esters by reaction with an alkyl halide, an alkylene halide, an aralkyl halide, a dialkyl sulphate or an aryl sulphonic acid ester, or the quaternary compound of the pyridine-3-acetic acid may be used as starting material. The operations of esterification and conversion into a quaternary compound may be performed in one operation. In examples: (1) a methanol solution of pyridine-3-acetic acid is boiled under reflux in the presence of hydrogen chloride. The solvent is removed and the product treated with sodium carbonate. Instead of the free acid, the acid amide may be used as starting material. To convert the pyridine-3-acetic acid methyl ester so prepared into its quaternary compound, it is boiled with methyl iodide under reflux to form pyridine-3-acetic acid methyl ester methiodide. Treatment of this compound with silver chloride forms the corresponding methochloride. Treatment of the methyl ester with dimethyl sulphate yields the dimethylsulphonate. Instead of dimethyl sulphate there may be used p-toluene sulphonic acid methyl ester. (2) As in example (1) using ethanol instead of methanol. (3) As in example (1) using as the esterifying alcohol isopropanol. (4) As in example (1) using isobutyl alcohol. (5) Pyridine-3-acetic acid is converted into its acid chloride with thionyl chloride and this compound esterified with n - propanol. (6) Pyridine-3-acetic acid methyl ester is treated with allyl alcohol in the presence of a small amount of sulphuric acid to form the pyridine-3-acetic acid allyl ester. (7) The dry sodium salt of pyridine-3-acetic acid is boiled with chlorethyldiethylamine to form pyridine-3-acetic acid diethylaminoethanol. (8) Pyridine-3-acetic acid is heated with excess of methyl iodide under reflux to form pyridine-3-acetic acid methyl ester methiodide. The Specification as open to inspection under Sect. 91 includes also the application of the process of the invention to aromatic and heterocyclic alcohols. This matter is not included in the Specification as accepted.
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
CH563171X | 1941-08-16 |
Publications (1)
Publication Number | Publication Date |
---|---|
GB563171A true GB563171A (en) | 1944-08-02 |
Family
ID=4520438
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
GB11226/42A Expired GB563171A (en) | 1941-08-16 | 1942-08-11 | Manufacture of pyridine-3-acetic acid esters and quaternary compounds thereof |
Country Status (1)
Country | Link |
---|---|
GB (1) | GB563171A (en) |
Cited By (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US2852519A (en) * | 1954-12-27 | 1958-09-16 | Phillips Petroleum Co | Method for producing esters of heterocyclic nitrogen carboxylic acids |
-
1942
- 1942-08-11 GB GB11226/42A patent/GB563171A/en not_active Expired
Cited By (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US2852519A (en) * | 1954-12-27 | 1958-09-16 | Phillips Petroleum Co | Method for producing esters of heterocyclic nitrogen carboxylic acids |
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