4-Benzyloxyaniline hydrochloride → (4-(Benzyloxy)phenyl)hydrazine monohydrochloride

Participants

Reaction Steps

p-Benzyloxyphenylhydrazine hydrochloride was prepared by the method of Mentzer, et al., [C.A. 48:33412]. Thus, p-benzyloxyaniline hydrochloride (72.6 g) was diazotized with conc. HCl (174 ml) and sodium nitrite (23.2 g) in water (40 ml) at 0° C. A solution of stannous chloride (169.3 g) in conc. HCl (435 ml) was added rapidly and the reaction mixture stirred for two hours. The solid product was filtered and washed with absolute ethanol, then partially dissolved in boiling methanol/ethanol (1:1) and filtered hot, yielding 52.5 g of p-benzyloxyphenylhydrazine hydrochloride.

Provenance & Evidence