Sulfuric Acid → 3,5-Dinitroaniline

Participants

Reaction Conditions

Reaction Steps

To a solution of 3,5-dinitrobenzoic acid (4.0 g, 18.9 mmol) in a mixture of concentrated sulfuric acid (6 mL), 30% fuming sulfuric acid (18 mL) and CHCl3 (25 mL) was added sodium azide (1.4 g, 21.7 mmol), in small portions. The resulting mixture was heated to reflux (80° C.) for 3 hours and then cooled to 25° C. after which it was poured on ice. An orange solid was isolated after vacuum filtration (3.25 g, 17.7 mmol, 94%). 1H NMR (300 MHz, CDCl3) δ 8.14 (t, J=1.8 Hz, 1H), 7.64 (d, J=1.8 Hz, 2H), 4.39 (s (br), 2H); 13C NMR (75 MHz, CDCl3) δ 151.9, 150.1, 113.1, 105.2; HRMS (ESI) Calculated for C6H4N3O4 [M−H]−: 182.0195. Found: 182.0207. m.p.: 113.1° C.

Provenance & Evidence