GB558774A - - Google Patents

Abstract

558,774. Heterocyclic substituted fatty acids and their amides. SOC. OF CHEMICAL INDUSTRY IN BASLE. Jan. 1, 1942, Nos. 25 and 26. Convention dates, Jan. 16, 1941, and Sept. 12, 1941. Sample furnished. [Class 2 (iii)] Heterocyclic substituted fatty acids and amides thereof are prepared by heating a heterocyclic-aliphatic ketone with an ammonium sulphide or with an amine in the presence of sulphur. Parent materials mentioned include pyridine alkyl ketones such as pyridines, methyl ketones, and pyridine ethyl ketones, quinoline alkyl ketones such as 2-acetyl quinoline 8-acetyl quinoline and 3-acetyl quinoline, and 1-phenyl-4 acetyl pyrazole, and substitution compounds of the above. The reaction is preferably carried out in the presence of water and/or an organic solvent such as dioxane. Amines mentioned include dimethylamine, diethylamine and piperidine. In examples (1) Aqueous ammonium sulphide and sulphur is added to a dioxane solution of 3- acetyl pyridine to give on heating under pressure to 160‹C. for 6 hours pyridine-3- acetamide. The mother liquors from the crystallization of this compound give an alkaline hydrolysis, pyridine-3-acetic acid. (2)3- acetyl pyridine, sulphur, and ammonium sulphide are heated in a bomb tube at 160‹C. for 12 hours to give pyridine-3-acetic acid. (3) 8-acetyl-quinoline, diethylamine and sulphur are heated for 5 hours to 150‹C. and the product saponified with alkali to give quinoline- 8-acetic acid.