Water → N-(2-Amino-5-nitropyridin-3-yl)-4-nitrobenzamide

Reaction equation

[NH2:1][C:2]1[C:7]([NH2:8])=[CH:6][C:5]([N+:9]([O-:11])=[O:10])=[CH:4][N:3]=1.[N+:12]([C:15]1[CH:23]=[CH:22][C:18]([C:19](Cl)=[O:20])=[CH:17][CH:16]=1)([O-:14])=[O:13].O>N1C=CC=CC=1>[NH2:1][C:2]1[C:7]([NH:8][C:19](=[O:20])[C:18]2[CH:17]=[CH:16][C:15]([N+:12]([O-:14])=[O:13])=[CH:23][CH:22]=2)=[CH:6][C:5]([N+:9]([O-:11])=[O:10])=[CH:4][N:3]=1

Participants

Procedure

To a solution of 2,3-Diamino-5-nitropyridine (3) in dry pyridine (85 mL) was added 4-nitrobenzoylchloride (0.875 g, 4.7 mmol) and the mixture was stirred at room temperature for 20 h. The mixture was then poured into H2O (250 mL) and stirred for 30 minutes. The resulting yellow solid was collected by filtration and rinsed with H2O until no pyridine remained. The solid was dried in vacuuo at 80 C to give 6 as a yellow solid (1.15 g, 3.8 mmol, 81%). 1H NMR (500 MHz, DMSO-d6) δ10.12 (br s, 1H), 8.83 (d, J=2.55 Hz, 1H), 8.84 (d, J=8.5 Hz, 2H), 8.35 (d, J=2.45 Hz, 2H), 8.24 (d, J=8.7 Hz, 2H), 7.62 (br s, 2H). EIMS M−1 302.3.