4-(2H-1,2,3,4-tetrazol-2-yl)aniline → 4-(2H-Tetrazol-2-yl)phenol

Participants

Reaction Steps

A suspension of 4-tetrazol-2-yl-phenylamine (5.4 g) in water (42 ml ) and conc sulphuric acid (10 ml) was added slowly to a solution of sodium nitrite (2.3 g) in water (8.5 ml) at 5°. The resulting green solution was stirred at this temperature for ca. 30 min, treated with a mixture of water (50 ml) and conc. sulphuric acid (67 ml) and heated to 120° for 1 h. Water (170 ml) was added, the reaction mixture cooled, saturated with brine (100 ml) and extracted with dichloromethane (3×100 ml), dried (Na2SO4) and evaporated to give the title compound as an orange solid (1.6 g).

Provenance & Evidence