Sodium Hydroxide → 3-Bromo-5-ethylpyridine

Participants

Reaction Conditions

Reaction Steps

Sodium hydroxide (10 g, 0.25 mol) and hydrazine monohydrate (10 mL) were added to a solution of 3-acetyl-5-bromopyridine (5 g, 25 mmol) dissolved in diethylene glycol (18 mL). The reaction mixture was heated to 140° C. for 6 hours and then partitioned between H2O and Ether. The organic layers were washed with brine, dried over MgSO4 and concentrated. The residue was purified by flash silica gel chromatography (0% to 40% EtOAc in hexanes) to give the title compound (3 g, 65%). 1H NMR (400 MHz, CDCl3): δ 1.26 (t, J=7.6 Hz, 3 H), 2.65 (q, J=7.6 Hz, 2 H), 7.67 (s, 1 H), 8.37 (s, 1 H), 8.51 (s, 1 H).

Provenance & Evidence