Stannous chloride dihydrate → 5-Bromo-2-(4-methoxyphenyl)pyridin-3-amine

Participants

Reaction Conditions

Reaction Steps

To a stirred mixture of 5-bromo-2-(4-methoxyphenyl)-3-nitropyridine (0.19 g, 0.60 mmol) in EtOAc (10 mL) was added tin(II) chloride dihydrate (0.67 g, 3.00 mmol) in portions. Upon complete addition of the reducing agent, the mixture was carefully heated to 70° C. After 20 h, the reaction was cooled to rt and diluted with ethyl acetate, then washed with 1M NaOH, water, and brine. After drying over anhydrous sodium sulfate and filtration, the organic solvent was removed under reduced pressure. The light yellow solid was identified as 5-bromo-2-(4-methoxyphenyl)pyridin-3-amine. 1H NMR (400 MHz, DMSO-d6) δ ppm 7.90 (1H, d, J=2.0 Hz), 7.57 (2H, d, J=8.8 Hz), 7.35 (1H, d, J=2.0 Hz), 7.01 (2H, d, J=8.8 Hz), 5.36 (2H, s), 3.80 (3H, s).

Provenance & Evidence