Sodium Hydroxide → 3-Amino-5-bromo-2-chloropyridine

Participants

Reaction Steps

To a stirred suspension of 5-bromo-2-chloro-3-nitropyridine (20.0 g, 84.2 mMol) in conc. HCl (90 mL) was added SnCl2.2H2O (60.0 g, 266 mMol) portionwise over 2 h. (The reaction got very warm to the touch.) The reaction was stirred at RT for 18 h, poured onto ice, and basified with aq. 6 N NaOH (300 mL). The resultant slurry was filtered, washed with H2O, and dried under vacuum to give the title compound (15.53 g, 89%) as an off-white solid: 1H NMR (400 MHz, DMSO-d6) δ ppm 7.66 (d, J=2.3 Hz, 1H), 7.30 (d, J=2.3 Hz, 1H), 5.90 (br.s., 2 H); MS (ES) m/e 206.7 (M+H)+.

Provenance & Evidence