反应详情

A mixture of 4-chloro-6-(4-nitrophenyl)-2-(4-phenoxyphenyl)nicotinonitrile (136.3 mg, 0.319 mmol), zinc dust (312 mg, 4.78 mmol), ammonium chloride (256 mg, 4.78 mmol), THF (3 mL) and methanol (3 mL) was stirred at room temperature for 15 min, and filtered. The filtrate was concentrated and partitioned with dichloromethane and saturated sodium bicarbonate. The organic layer was separated and concentrated. Silica gel chromatography, eluting with 0-40% ethyl acetate in hexanes, gave pure 6-(4-aminophenyl)-4-chloro-2-(4-phenoxyphenyl)nicotinonitrile as yellow solid (51 mg). 1H NMR (400 MHz, CDCl3) δ ppm 7.96-8.04 (4H, m), 7.70 (1H, s), 7.40 (2H, t, J=8.03 Hz), 7.18 (1H, t, J=7.40 Hz), 7.08-7.14 (4H, m), 6.76 (2H, δ, J=8.78 Hz), 4.04 (2H, s); MS (ES+) m/z: 398 (M+H); LC retention time: 4.551 min (analytical HPLC Method A). Additional impure product was also obtained from the chromatography (48.1 mg).

1. filtrationfiltered
2. concentrationThe filtrate was concentrated
3. custompartitioned with dichloromethane and saturated sodium bicarbonate
4. customThe organic layer was separated
5. concentrationconcentrated
6. washSilica gel chromatography, eluting with 0-40% ethyl acetate in hexanes