Ammonium Chloride → 3-Chloro-N2-phenylbenzene-1,2-diamine

Participants

Reaction Steps

To a mixture of (2-chloro-6-nitrophenyl)phenylamine (676 mg, 2.72 mmol) in MeOH (45 mL) and water (15 mL) were added NH4Cl (872 mg, 16.31 mol) and iron powder (607 mg, 10.87 mmol) and the reaction mixture was heated to reflux temperature for 4 h. After cooling to RT, the solid was filtered through a pad of Celite® and washed with additional MeOH. The filtrate was concentrated in vacuo and then partitioned between EtOAc and water. The aqueous phase was further extracted with EtOAc and the combined organic layers were washed with brine, then dried (Na2SO4) and concentrated in vacuo. The resulting residue was purified by column chromatography (Si—PCC, gradient 50-100% DCM in cyclohexane). The product containing fractions were concentrated in vacuo affording 3-Chloro-N2-phenylbenzene-1,2-diamine as a pale orange solid (500 mg, 84%). LCMS: RT 3.45 min [M+H]+ 219.1.

Provenance & Evidence