[K].Cl[C:3]1[N:11]=[CH:10][CH:9]=[CH:8][C:4]=1[C:5]([O-:7])=[O:6].[N+:12]([C:15]1[CH:16]=[C:17]([CH:19]=[CH:20][CH:21]=1)[NH2:18])([O-:14])=[O:13].C(N1CCOCC1)C.Cl>CN(C)C=O>[N+:12]([C:15]1[CH:16]=[C:17]([CH:19]=[CH:20][CH:21]=1)[NH:18][C:3]1[C:4]([C:5]([OH:7])=[O:6])=[CH:8][CH:9]=[CH:10][N:11]=1)([O-:14])=[O:13]Potassium-2-chloro-nicotinate (89 g, 455 mmole) was suspended in 630 ml of dimethylformamide. To this suspension was added 3-nitroaniline (75.3 gm, 546 mmole), cupric acetate (5.1 g, 25.5 mmole) and N-ethyl morpholine (52.3 g, 455 mmoles). The suspension was refluxed with stirring under N2 for 4 hours. The reaction mixture was cooled to room temperature and the pH was adjusted to 4-5 by the addition of 6M HCl. A yellow precipitate was isolated from the reaction mixture, washed with water and air dried yielding 66.3 g (256 mmole, 56% yield) of 2-(3-nitroanilino)-3-carboxypyridine (mp 262°-264° C.).
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