N-bromobutanimide → 2-Amino-5-bromo-4-chloropyridine

Participants

Reaction Conditions

Reaction Steps

To a stirred solution of 2-amino-4-chloropyridine (1 g) in acetonitrile (8 mL) was added dropwise a solution of N-bromosuccinimide (1.5 g) in acetonitrile (2 mL). The reaction mixture was stirred at 25-28° C. for 1 h. The solvent was evaporated, then the residue was suspended in water and extracted with dichloromethane (2×20 mL). The organic layer was dried over anhydrous sodium sulphate, filtered and concentrated under vacuum. The resulting crude material was purified by column chromatography, using 100-200 mesh size silica and 10-25% EtOAc in hexane as eluent, to give the title compound (1 g) as a yellow solid. δH (400 MHz, CDCl3) 8.16 (s, 1H), 6.62 (s, 1H), 4.55 (br s, 2H). LCMS: m/z 208.9, RT 2.19 minutes.

Provenance & Evidence