Hydrazine hydrate (1:1) → 2-Hydrazinyl-3-methylpyridine

Participants

Reaction Conditions

Reaction Steps

2-Bromo-3-methylpyridine (5.16 g, 30.00 mmol) and hydrazine hydrate (10.92 mL, 224.97 mmol) were mixed. The reaction was heated to 110° C. for 20 hours with stirring. The mixture was cooled to ambient temperature during which a white solid precipitated. This was then collected filtration, washed with ether (3×10 mL), slurried in DCM (50 mL), stirred for 10 minutes and then passed through a phase separation cartridge to remove water. The organic liquors were evaporated and dried under high vacuum to give 2-hydrazinyl-3-methylpyridine (2.5 g, 68%). 1H NMR (400 MHz, CDCl3) δ 2.08 (3H, s), 4.02 (2H, s), 5.50 (1H, s), 6.64 (1H, dd), 7.20-7.30 (1H, m), 8.08 (1H, dd). MP=119° C. (Lit 122° C.).

Provenance & Evidence