5-Bromo-3-nitropyridine-2-carbonitrile → 3-Amino-5-bromopyridine-2-carbonitrile

Participants

Reaction Conditions

Reaction Steps

Iron powder (5.0 g, 90 mmol) was added to a solution 5-bromo-3-nitropyridine-2-carbonitrile (4.56 g, 20 mmol) in glacial acetic acid (125 ml). The suspension was stirred for 2 h at 80° C. The cooled mixture was filtered through a short plug of Celite and washed with EtOAc. Solvents were evaporated, the residue was dissolved in EtOAc and neutralised with 20% aqueous K2CO3. Phases were separated and organic phase was washed with water and brine, dried over anhydrous Na2SO4, filtered and evaporated. Crude product was purified by CombiFlash (DCM-MeOH, gradient elution). Product fractions were combined and evaporated to produce 1.67 g of product. 1H-NMR (400 MHz; d6-DMSO): δ 6.55 (s, 2H), 7.46 (d, 1H, J=2.0 Hz), 7.94 (d, 1H, J=1.9 Hz).

Provenance & Evidence