Trichloromethylquinolines : Synthesis and Reaction with Trimethyl Phosphite

Abstract

Heating of methylquinolines (1, 3, 6, and 12) with phosphorus pentachloride in phosphoryl chloride gave the corresponding trichloromethylquinoline derivatives (2, 4, 9, and 14). Similar treatment of 4-chloro-2-methyl-3-nitroquinoline (16) gave 4-chloro-2-dichloromethyl-3-nitroquinoline (17), 4-chloro-3-nitro-2-trichloromethylquinoline (18), and 3, 4-dichloro-2-cyanoquinoline (19). The reaction of 2-trichloromethylquinolines (2, 9, and 18) with trimethyl phosphite gave the corresponding methylated products, 2-(1, 1-dichloroethyl) quinolines (21, 24, and 27). However, 4-trichloromethylquinolines (4 and 14) reacted with trimethyl phosphite under similar conditions to give 4-dichloromethylquinolines (23 and 13).