N-[4-(1,1-dimethylethyl)-2-nitrophenyl]acetamide → 4-tert-Butyl-2-nitroaniline

Participants

Reaction Steps

A reactor was charged with methanol (13.5 L) and N-(4-tert-butyl-2-nitrophenyl) acetamide (Preparation 109, 7.0 kg, 29.6 mol). The mixture was stirred for ten minutes then a solution of 30% sodium methoxide in methanol (6.49 L, 35.5 mol) was added slowly at room temperature. The mixture was heated slowly to reflux and held at that temperature for two hours. The methanol was distilled to dryness under vacuum at 50-55° C. and the solids cooled to room temperature. The residue was stirred in water (35 L) for one hour and the solids collected by filtration, washed with water (14 L), and dried at 45-50° C. to provide 5.3 kg of the title compound.

Provenance & Evidence