Methanol → 6-bromo-N1-methylbenzene-1,2-diamine

Participants

Reaction Conditions

Reaction Steps

A mixture of (2-bromo-6-nitrophenyl)methylamine (4.16 g, 18 mmol), ammonium chloride (5.6 g, 108 mmol) and iron powder (4.09 g, 72 mmol) in H2O (32 mL) and MeOH (80 mL) was stirred vigorously for 5 h at 90° C. After cooling to RT, the reaction mixture was filtered through Celite®, washed with MeOH/DCM and the filtrate concentrated in vacuo. The resulting residue was taken up in EtOAc (75 mL) and washed with H2O (75 mL). The aqueous was further extracted with EtOAc (2×75 mL). The combined organic fractions were washed with brine (50 mL), dried (Na2SO4) and concentrated in vacuo. The resulting residue was purified by column chromatography (Si—PPC, gradient 10-75% EtOAc/cyclohexane) to afford the title compound as a red oil (1.46 g, 40%). LCMS (Method C): RT 1.79 min [M+H]+ 211 (for 79Br). 1H NMR (CDCl3, 400 MHz): δ 6.92 (1H, dd, J=8.0, 1.5 Hz), 6.75 (1H, dd, 8.0, 8.0 Hz), 6.64 (1H, dd, J=8.0, 1.5 Hz), 4.02 (2H, bs), 3.25 (1H, bs), 2.68 (3H, s).

Provenance & Evidence