Methanol → 3-Amino-5-bromopyridine-2-carboxamide

Participants

Reaction Conditions

Reaction Steps

Tin chloride (90 g, 400 mmol) was added to a solution of 5-bromo-3-nitropicolinonitrile (17 g, 74 mmol) in methanol (800 mL) and the reaction was heated to 40° C. for 4.75 h. The solvent was removed in vacuo and toluene added and removed in vacuo. The crude was suspended in EtOAc and the mixture basified to pH 8 with saturated NaHCO3 (aq). The organic layer was separated and the aqueous slurry extracted with CHCl3 (×3). The combined organics were filtered through Celite, dried (MgSO4) and concentrated in vacuo to give crude 3-amino-5-bromopyridine-2-carboxamide which was used directly without further purification.

Provenance & Evidence