Acetic Acid → 5-Bromo-6-chloropyridin-3-amine

Participants

Reaction Steps

To a stirred mixture of 3-bromo-2-chloro-5-nitropyridine (10.00 g, 42.1 mmol) and acetic acid (12.16 mL, 211 mmol) in water (100 mL) at 0° C. was added iron (11.76 g, 211 mmol, powder −325 mesh). The mixture was warmed to room temperature and stirred for 4 h. The reaction mixture was filtered and washed with water. The filtrate was then extracted with EtOAc. The filter cake was then washed with EtOAc, and the resulting filtrate was combined with the previous organic layer from the aqueous extraction. The two organic mixtures were then washed with water (2×), washed with sat. sodium chloride, dried over magnesium sulfate, filtered, and concentrated to give 5-bromo-6-chloropyridin-3-amine. MS (ESI, pos. ion) m/z: 207.9 and 209.9 (M+1).

Provenance & Evidence