New derivatives of 4-quinaldinol

The reactions of 1, 1, 3-trichloro-1-propene and also 1, 1, 1-trichloro-2-propene with acetoacetic ester gave -(, -dichlorallyl)acetoacetic ester (I). In the reactions with aniline and o- and p-toluidines, the corresponding -(, -dichloroallyl)--arylamino-crotonic esters were produced, thermal cyclization of which gave 2-methyl-3-(, -dichloroallyl)-4-hydroxyquinoline (II) and its 6CH₃- (III) and 8CH₃- (IV) homologs. With phosphorus oxychloride, II–IV gave the corresponding 4-chloro-substituted quinolines (V–VII); with concentrated sulfuric acid, II–VII were converted into the corresponding -quinolinylpropionic acids VIII–XIII.For part XI, see 5].