Oxidative replacement of the hydrazino-group by hydrogen and deuterium in azanaphthalenes

Abstract

Comparison of methods for replacing a hydrazino-group by a hydrogen atom in the quinoline, isoquinoline, phthalazine, quinazoline, and pteridine series has shown that the most useful reagents are (a) oxygen and ethanolic alkali, and (b) aqueous cupric sulphate. This replacement has been adapted to the synthesis of monodeuteriated quinolines and isoquinolines, and the n.m.r. spectra of these are discussed. Ultraviolet spectra and ionisation constants for all hydrazinoquinolines in water are discussed. An unusual reaction of hydrazine with 7-chloro-8-nitroquinoline is noted.