Hydrazine → 2-Bromo-6-hydrazinopyridine

Participants

Reaction Steps

A mixture of 2,6-dibromopyridine (1.44 g, 6.1 mmol) and hydrazine (1.65 mL, 32.2 mmol) in butanol (100 mL) was stirred at reflux for 18 hours. The reaction mixture was cooled to room temperature and concentrated under reduced pressure. The residue was partitioned between an aqueous saturated solution of sodium bicarbonate and EtOAc. The organic layer was separated and washed with brine, dried over Na2SO4, filtered and concentrated to give (6-Bromopyridin-2-yl)hydrazine as a white solid (1.0 g, 92%). 1H NMR (400 MHz, CHCl3-d): δ 7.36-7.28 (m, 1 H); 6.82 (d, J=7.70 Hz, 1 H); 6.67 (d, J=7.7 Hz, 1 H); 5.97 (s, 1 H); 3.80 (s, 2 H).

Provenance & Evidence