Abstract
Methyl groups at the 4-position of 2, 4-dimethyl-, 2, 4, 6-trimethyl-pyridine, 2, 4-dimethyl-, 2, 4, 6-trimethyl-pyrimidine, 2, 4-dimethylquinoline, and 2, 4-dimethylquinazoline were nitrosated selectively with ethyl nitrite in the presence of alkali amide in liquid ammonia to give the corresponding 4-aldoximes. On heating with phosphoryl chloride, the aldoximes were converted to 4-carbonitriles except 2-methylquinazoline-4-aldoxime which was sublimated with phosphorous pentoxide to afford 4-cyano-2-methylquinazoline. Related to these synthetic experiments, the hydrogen-deuterium exchange reaction of the methyl groups was examined by means of the NMR technique. The observed results did not contradict the direction of nitrosation of the testing compounds.
