Hydrochloric Acid → 2-(3-Nitroanilino)-3-carboxypyridine

Participants

Reaction Steps

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.).

Provenance & Evidence