4-Chloro-2,6-dinitroaniline → 5-Chloro-3-nitro-1,2-benzenediamine

Participants

Reaction Conditions

Reaction Steps

A suspension of 4-chloro-2,6-dinitroaniline (0.261 g, 1.19 mmol, Aldrich, used as received) in 6.66% aq. (NH4)2S (8.0 mL, prepared from 20% aq. solution available from Aldrich) and ethanol (8.0 mL) was refluxed for 45 min during which time it formed dark red solution. It was then cooled to 28° C. and the precipitated solid was filtered and dried under vacuum to yield 146 mg (65%) of pure 5-chloro-3-nitro-1,2-phenylenediamine as a shining red solid, 1H NMR (DMSO-d6): 5.031 (br s, 2H), 6.687 (br s, 2H), 6.912 (d, 1H, J=2.4 Hz), 7.413 (d, 1H, J=2.1 Hz).

Provenance & Evidence