Twofold alkylations of ketone and aldehyde phenylhydrazones with methylene halides by means of alkali amides to form bis-N-derivatives

The phenylhydrazones of benzophenone, acetophenone, and benzaldehyde were converted by a molecular equivalent of an alkali amide in liquid ammonia to their mono-alkali derivatives, which underwent twofold alkylation with 1,3-dibromopropane or higher methylene halides or with α,α′-dichloro-p-xylene to form corresponding bis-N-derivatives. Two of the products were reduced by means of lithium in liquid ammonia to give corresponding substituted bis-hydrazines. These reactions furnish convenient methods of synthesis of such compounds.