Abstract
It has already been reported that the thermal reaction of safrole or methyleugenol with acid amide, in the presence of phosphoryl chloride, resulted in the formation of an isoquinoline derivative. The use of aliphatic or aromatic aldoxime, in place of acid amide, was found to give 1-substituted 3-methyl-6, 7-dimethoxy (or methylenedioxy)-3, 4-dihydroisoquinoline. The isoquinoline derivative was obtained in approximately 30% yield when 1 mole each of allylbenzene and aldoxime mixture was allowed to react in an ice bath, allowed to stand for some time at a room temperature, then allowed to boil gently in a water or an oil bath, decomposed with ice water, impurities such as safrole and methyleugenol removed, and the basic substance collected. The aldoximes used were acetaldoxime, benzaldoxime, anisaldoxime, veratraldoxime, and piperonaldoxime. By this means, 3, 4-dihydroneupaverine could be obtained by a single process.
