Catalytic hydrogenation of C=N bond Communication 1. Study of hydrogenation of azomethines of benzylidene series

Abstract

1. The hydrogenolysis of benzylideneaniline, and of its methyl and methoxy derivatives, in the presence of Pd/C proceeds selectively: the hydrogenolysis of the benzyl-N bond begins only after the absorption of the first mole of hydrogen. 2. Partial hydrolysis of the C=N double bond occurs under the hydrogenation conditions due to traces of water in the solvent. 3. The insertion of electron-donor substituants into the benzene ring, attached to the nitrogen, has little effect on the hydrogenation rate of the azomethine. The o-substituted azomethines hydrogenate somewhat faster than do the m- and p-substituted derivatives.