Hydrochloric Acid → 3-(2H-tetrazol-5-yl)-phenylamine hydrochloride

Participants

Reaction Steps

To a solution of 5-(3-nitrophenyl)tetrazole (22 g, 0.12 mol) in ethanol (500 mg) was added 10% palladium on carbon (1.5 g, 7% (w/w)) in hydrochloric acid (23 mg of a 5M solution). The mixture was hydrogenated at 40 psi for 10 min, then the catalyst filtered off and washed with water. The solvents were evaporated in vacuo and the brown solid azeotroped with toluene (4×100 mg). The resulting solid was triturated with hot ethanol to give 5-(3-aminophenyl)tetrazole hydrochloride (16.3 g, 71%) as a beige powder, mp 203°-205° C. 1H NMR (360 MHz, D2O) δ 7.63 (1H, d, J=9 Hz), 7.75 (1H, t, J=8 Hz), 8.00 (2H, m).

Provenance & Evidence