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

Participants

Reaction Steps

A mixture of 2,5-dibromopyridine (44.2 g, 0.187 moles), 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 is refluxed gently for 29 hours. The mixture is then cooled and stirred for 20 hours. To the resulting slurry, cold water (220 mL) is added. The slurry is stirred for an additional 30 minutes and filtered. The cake is washed with cold water (3×) and dried in a vacuum-oven (40-45° C.) for 48 hours. The title compound (30.5 g, 87%) is obtained as off-white flakes.

Provenance & Evidence