[NH2:1][C:2]1[C:7]([NH:8][C:9](=O)[C:10]2[CH:15]=[CH:14][C:13]([N+:16]([O-:18])=[O:17])=[CH:12][CH:11]=2)=[CH:6][C:5]([N+:20]([O-:22])=[O:21])=[CH:4][N:3]=1.O>C(O)CO.Cl>[N+:20]([C:5]1[CH:6]=[C:7]2[N:8]=[C:9]([C:10]3[CH:15]=[CH:14][C:13]([N+:16]([O-:18])=[O:17])=[CH:12][CH:11]=3)[NH:1][C:2]2=[N:3][CH:4]=1)([O-:22])=[O:21]To a stirred suspension of N-(2-Amino-5-nitropyridin-3-yl)-4-nitrobenzamide (6) (1.15 g, 3.8 mmol) in ethylene glycol (75 mL) was added HCl (Conc., 3 drops) and the mixture heated at 160° C. for 6 h. The solution was cooled to room temperature and poured into H2O (200 mL) and the resulting solid collected by filtration, rinsed with H2O, and dried in vacuo at 80° C. to give 4 as a pale yellow solid (1 g, 3.5 mmol, 92%). 1H NMR (500 MHz, DMSO-d6) δ14.58 (br s, 1H), 9.28 (apparent d, 1H), 8.88 (br s, 1H), 8.51 (d, J=8.39 Hz, 2H), 8.45 (d, J=8.28 Hz, 2H). EIMS M−1 284.3. Rf=0.55 (silica, 19:1 DCM/MeOH)
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