Ethanol → 3-Methyl-4-nitrobenzene-1,2-diamine

Participants

Reaction Steps

To a solution of 3-methyl-2,4-dinitroaniline (30 g, prepared by the procedure of A. J. Boulton, P. B. Ghosh, A. R. Katritzky, J. Chem Soc. (B), 1011 (1966)) in boiling ethanol (750 mL) is added dropwise over 90 minutes a solution of sodium sulfide nonahydrate (109.6 g) in water (750 mL). At the end of the addition, the mixture is refluxed for 30 minutes then poured in ice (2000 g) and allowed to stand until all the ice has melted. The mixture is then extracted with methylene chloride and the organic layer is dried over magnesium sulfate and rotary evaporated. The residue is purified by flash chromatography on silica gel, eluting with methylene chloride to afford 2,3-diamino-6-nitrotoluene as an orange solid.

Provenance & Evidence