3-(tert-Butyl)aniline hydrochloride → (3-Tert-butylphenyl)hydrazine

Participants

Reaction Steps

3-t-Butylaniline hydrochloride (5 g) in concentrated hydrochloric acid (8 ml) was stirred at 0° whilst a solution of sodium nitrite (1.86 g) in water (2.4 ml) was slowly added. The mixture was kept at 0° for 1 hour and, after filtering (at 0°), it was treated dropwise with a solution of stannous chloride dihydrate (18.2 g) in concentrated hydrochloric acid (18.8 ml). A pink-coloured solid separated. After 1 hour, this solid was filtered off and washed with saturated aqueous sodium chloride. The resulting salt was converted into base in the usual way to give 3-t-butylphenylhydrazine, b.p. 88°-90°/0.25 mm Hg.

Provenance & Evidence