2-Amino-3,5-dinitropyridine → 5-Nitropyridine-2,3-diamine

Participants

Reaction Steps

To a stirred suspension of 2-Amino-3,5-dinitropyridine (2) (1.62 g, 8.8 mmol) in MeOH (75 mL) was added an aqueous solution of (NH4)2S (20%, 15 mL, 44 mmol) dropwise at room temperature over 20 minutes. The mixture was stirred for an additional 30 minutes at room temperature and then heated at reflux for 30 minutes. The solution was cooled to room temperature and the solid collected by filtration, rinsed with cold MeOH (2×20 mL), and dried in vacuo at room temperature to give 3 as a red solid (0.812 g, 5.27 mmol, 60%). 1H NMR (500 MHz, DMSO-d6) δ 5.31 (s, 2H), 6.98 (s, 2H), 7.35 (d, J=2.55 Hz, 1H), 8.28 (d, J=2.91 Hz, 1H). EIMS M+1 155.1.

Provenance & Evidence