Manufacture of derivatives of 2-phenyl-quinoline-4-carboxylic acids

摘要

Esters of 2-phenylquinoline-4-carboxylic acid, its homologues and substitution products are prepared by esterifying the acids with glycerol or halohydrins of glycerol. When the products contain halogen, they may be reacted with a further quantity of the acids or their salts. The products may be used therapeutically. According to the examples, (1) the a -monoglycerol ester of 2-phenylquinoline-4-carboxylic acid is prepared by heating the acid with glycerol in the presence of sulphuric acid, or by treating the acid chloride with glycerol or the potassium salt with a -monochlorhydrin; the glycerol esters of 2-phenyl-6-methoxy-quinoline-4-carboxylic acid and 2-p-tolyl-quinoline - 4 - carboxylic acid are prepared similarly; (2) a a 1-bis-(2 - phenylquinoline-4-carboxylic acid)-glycerol ester is obtained by reacting potassium 2 - phenylquinoline - 4 - carboxylate with a -dichlorhydrin or with 2-phenylquinoline - 4 - carboxylic acid - ( -g chlorpropandiol)-a -ester, or by heating 2 mols. of the acid chloride with 1 mol. of glycerol; the a a 1-bis-glycerol esters of the 6-methoxy and 2-p-tolyl acids are similarly prepared; the a b -bis-(2-phenylquinoline-4-carboxylic acid)-glycerol results when b -dichlorhydrin is employed; (3) a b g - tri - (2 - phenylquinoline - 4 - carboxylic acid)-glycerol ester is formed when potassium 2-phenylquinoline-4-carboxylate is heated with 2 - phenylquinoline - 4 - carboxylic acid - b b 1-dichlorisopropyl ester; (4) 2-phenylquinoline-4-carboxylic acid chloride when heated with a -monochlorhydrin gives 2-phenylquinoline-4-carboxylic acid-g -chlorpropandiol-a ester, and with a -dichlorhydrin yields 2-phenylquinoline 4-carboxylic acid - b b 1 - dichlorisopropyl ester; the 2-p-tolylquinoline-4-carboxylic acid-b b 1-dichlorisopropyl ester is similarly prepared; a b - bis - (2 - phenylquinoline - 4 - carboxylic acid)-g -chlorpropandiol ester results from the interaction of 1 mol. of a -monochlorhydrin on 2 mols. of the acid chloride.