Sodium Hydroxide → 3-Amino-5-bromo-2-chloropyridine

Participants

Reaction Steps

A suspension of 5-bromo-2-chloro-3-nitropyridine (Combi-Blocks, San Diego, USA, 41.3 mmol) in concentrated HCl (45 ml) was cooled with an ice-bath. Was added portionwise over 1.5 h SnCl2 dihydrate (124 mmol). The RM was stirred for 24 h at rt then poured on ice and basified with 6 M aqueous NaOH (125 ml). The resulting slurry was filtered and the solid was taken in aqueous NaHCO3, sonicated and filtered. The solid was dissolved in EtOAc and water and the aqueous layer was separated and extracted with EtOAc. The combined organic layers were washed with water, brine, dried over Na2SO4, filtered and evaporated to give the title compound as an off-white solid. (HPLC: tR 2.52 min (Method A); M+H=207 (BrCl pattern) MS-ES)

Provenance & Evidence