(+-)-2-Butanol → 5-Bromo-2-hydrazinopyridine

Participants

Reaction Steps

A mixture of 2,5-dibromopyridine (44.2 g, 0.187 mol), hydrazine hydrate (55% by weight, 105.7 mL, 1.87 mol), poly(ethylene glycol) (187.0 mL), 2-butanol (37.3 mL) and water (187.0 mL) under nitrogen was refluxed gently for 29 hours. The mixture was cooled and stirred for 20 hours. To the resulting slurry, cold water (220.0 mL) was added. The slurry was stirred for an additional 30 minutes and filtered. The cake was washed with cold water (3×) and dried in a vacuum-oven (40–45° C.) for 48 hours. The title compound (30.5 g, 87%) was obtained as off-white flakes.

Provenance & Evidence