Ammonia → HCID 70896199, compound

Participants

Reaction Steps

A solution of cyanogen bromide (5.0 mL, 5 M in acetonitrile, 25 mmol) was added to a mixture of methyl 3,4-diaminobenzoate (3.0 g, 18 mmol) in water (50 mL). The reaction was stirred at room temperature overnight. Aqueous ammonia (20 mL) and ethyl acetate (100 mL) were added to the reaction mixture and the layers were separated. The organics were dried over sodium sulfate, filtered, and concentrated. To the crude residue was added 2 N aqueous hydrochloric acid (18 mL, 36.0 mmol) and the mixture was heated at reflux overnight. The reaction was concentrated to give the title compound (2.90 g, 97%). 1H NMR (400 MHz, DMSO-d6, δ): 8.75 (s, 2 H), 7.84 (s, 1 H), 7.77 (dd, J=1.2 Hz, J=8.4 Hz, 1 H), 7.38 (d, J=8.4 Hz, 1 H).

Provenance & Evidence