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

Participants

Reaction Steps

To a solution 3-methyl-2,4-dinitroaniline (30 g) 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 heated to reflux for 30 minutes then poured into 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 get, eluting with methylene chloride to afford 2,3-diamino-6-nitrotoluene as an orange solid.

Provenance & Evidence