Ammonium Chloride → 4-Methoxy-o-phenylenediamine

Participants

Reaction Steps

To a solution of 4-methoxy-2-nitroaniline (10 g, 59.4 mmol) in EtOH (200 mL) and water (80 mL) was added iron (12 g, 210 mmol) and ammonium chloride (9.63 g, 180 mmol). The mixture was then heated to reflux and stirred overnight. The mixture was filtered and the filtrate was evaporated to remove the EtOH and the residue was purified by flash chromatography on silica gel column (elution with DCM/MeOH=80:1) to give 4-methoxybenzene-1,2-diamine (intermediate 35) (5.65 g, 69%) as a yellow solid.

Provenance & Evidence