4-Bromo-2-methyl-6-nitroaniline → 5-Bromo-3-methylbenzene-1,2-diamine

Participants

Reaction Steps

To a stirred solution of compound 4-bromo-2-methyl-6-nitroaniline (5.0 g) in EtOH (85 ml) and water (43 ml) were added iron powder (6.0 g) and CaCl2 (4.8 g) at room temperature and the resulting reaction mixture was then heated at reflux for 4 h. The mixture was then cooled to room temperature, filtered through Celite, and washed with EtOH. The filtrate was concentrated and the resulting residue was diluted with DCM. The DCM layer was successively washed with water and brine, dried over Na2SO4 and concentrated in vacuo to give the title compound (4.0 g) as a dark brown solid.

Provenance & Evidence