Abstract
4-Methylquinoline, when treated with chlorine in carbon tetrachloride, undergoes addition reaction to give 5, 6, 7, 8, 8-pentachloro-5, 6, 7, 8-tetrahydro-4-methylquinoline. Similarly, 2-chloro-4-methylquinoline and 4-chloro-2-methylquinoline undergo addition reaction to give 2, 5, 6, 7, 8-pentachloro-5, 6, 7, 8-tetrahydro-4-methylquinoline and 4, 5, 6, 7, 8, 8-hexachloro-5, 6, 7, 8-tetrahydro-2-methylquinoline, respectively. On the other hand, similar chlorination of 2-ethoxy-4-methylquinoline gives 6, 8-dichloro-2-ethoxy-4-methylquinoline and 3, 6-dichloro-4-methylcarbostyril. Ch1orination of 2-chloroquinoline gives 2, 5, 6, 7, 8-pentachloro-5, 6, 7, 8-tetrahydroquinoline but that of 4-chloroquinoline or quinoline gives mainly 3, 4, 6, 8-tetrachloroquinoline.
