m-Chloroperbenzoic acid → 3-Chloro-4-cyano-5-(4-phenoxyphenyl)pyridine 1-oxide

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Reaction Steps

A solution of 3-chloro-5-(4-phenoxyphenyl)isonicotinonitrile (0.495 g, 1.614 mmol) and 77% 3-chloroperbenzoic acid (1.808 g, 8.07 mmol) in dichloromethane (20 mL) was stirred at room temperature. After 22 h at room temperature, the mixture was diluted with dichloromethane (100 mL), washed with 1 M sodium sulfite (25 mL), 1 N NaOH (2×25 mL), brined (25 mL), dried (MgSO4) and concentrated. Silica gel chromatography, loading with dichloromethane and eluting with 20-50% ethyl acetate in hexanes, gave 3-chloro-4-cyano-5-(4-phenoxyphenyl)pyridine 1-oxide as white solid (328.8 mg, 63% yield). 1H NMR (400 MHz, CDCl3) δ ppm 8.25 (1H, δ, J=1.51 Hz), 8.16 (1H, δ, J=1.51 Hz), 7.46-7.58 (2H, m), 7.36-7.45 (2H, m), 7.21 (1H, t, J=7.40 Hz), 7.03-7.16 (4H, m); MS (ES+) m/z: 323 (M+H); LC retention time: 3.863 min (analytical HPLC Method A).

Provenance & Evidence