5-bromo-N-methyl-2-nitroaniline → 5-BROMO-N1-METHYLBENZENE-1,2-DIAMINE

Participants

Reaction Steps

An orange solution consisting of 5-bromo-N-methyl-2-nitroaniline (1-2, 10.5 g, 45.4 mmol) in Acetic acid (200 ml) was treated with Zinc dust (8.92 g, 136 mmol, 3.0 eq), generating a mild exotherm. The cloudy maroon reaction mixture was capped and stirred for 20 min. The reaction was >80% complete, so an additional amount of Zinc dust (1.0 g, 16 mmol, 0.35 eq) was added and the reaction was stirred for 15 min. LC/MS showed complete reduction, so the reaction mixture was filtered through Celite and washed with MeOH. The residual filtrate was concentrated in vacuo, then partitioned between EtOAc (2×300 ml) and saturated aqueous NaHCO3 (350 ml). The combined organic layers were dried over Na2SO4 and concentrated, affording the title compound, 4-bromo-N2-methylbenzene-1,2-diamine (1-3), as a brown solid with >90% purity. LRMS m/z: Calc'd for C7H9BrN2 (M+H) 202.1, found 202.8.

Provenance & Evidence