Ammonia → 2-Amino-6-nitrophenol

Participants

Reaction Conditions

Reaction Steps

A suspension of 2,6-dinitrophenol (5 g), ammonia (3 ml) and ammonium chloride (14.30 g) in water (30 ml) was heated to 70° C. A solution of sodium sulphide nonahydrate (24.19 g) in water (23 ml) was added and the resulting mixture stirred at 70° C. for 2 hours. The reaction was cooled to room temperature, acidified (pH 3.2) with 2N HCl, and the brown precipitate isolated by filtration. The filtrate was extracted with chloroform (6×75 ml), the organic extracts combined with the precipitate, and evaporated in-vacuo to yield a dark brown solid. The solid was purified by flash chromatography (SiO2; dichloromethane) to yield the title compound (2.86 g, 68%) as a brown solid. δH (250 MHZ;d6DMSO), 6.75 (1H,td,ArH), 6.90 (2H,bs,ArNH2), 6.92 (1H,m,ArH), 7.14 (1H,m,ArH).

Provenance & Evidence