2-Amino-4-methyl-3,5-dinitrobenzonitrile → HCID 53405225, compound

Participants

Reaction Conditions

Reaction Steps

A mixture of 4-methyl-3,5-dinitrobenzonitrile (5) (50 g, 0.225 mmol), 5% palladium on carbon (10.0 g of 50% wet) and acetonitrile (400 ml) is hydrogenated under a hydrogen atmosphere (about 40 psi) at a temperature of about 30° C. for about 5 hours. The mixture is then filtered through a bed of Celite and the filter cake is washed with acetonitrile (about 200 mL). To a portion (about 400 mL) of the resulting solution is added water (about 400 mL) and the pH of the resulting mixture is adjusted to about 4.9 with 6N aqueous hydrochloric acid. The resulting mixture is then heated to about 40° C. and a stream of air is bubbled through the solution for about 18 hours. The pH of the resulting mixture is then adjusted again to about 5 with 6N aqueous hydrochloric acid and the temperature is held at about 40° C. for about another 2 hours. The mixture is then cooled to ambient temperature and the resulting solid is filtered, washed with water (500 mL), acetonitrile (200 mL) and dried to provide 2,3,7-triamino-4,6-dimethyl-1,9-phenazinedicarbonitrile (2) (19.44 g, about 85% Yield), as a dark red solid.

Provenance & Evidence