Abstract
Fusion reaction of methyl salicylate and secondary amines afforded salicylamide compounds in a low yield only in the case of 1, 2, 3, 4-tetrahydroisoquinoline (I) and piperidine, and the amide compound was not obtained in the case of 1, 2, 3, 4-tetrahydroquinoline (II), N-methylbenzylamine (III), N-methylaniline (IV), and diphenylamine (V), forming N-methylated tertiary amines as the main product. Further, when such tertiary amines were 2-methyl-1, 2, 3, 4-tetrahydroisoquinoline (VII) and N, N-dimethylbenzylamine, quaternary ammonium salicylate was also formed. When the secondary amine was a comparatively strong base like I, salicylate of I was also found to be formed as a by-product.
