O-Toluidine → HCID 66926890, compound

Participants

Reaction Conditions

Reaction Steps

A mixture of 3,5-dichloro-2-fluoroisonicotinonitrile (1.00 g, 5.24 mmol) and o-toluidine (10 g, 93 mmol) was heated to 150° C. for 20 h. After cooling to room temperature, the mixture was diluted with ethyl acetate (200 mL), washed with 1 N HCl (2×20 mL), saturated sodium bicarbonate (20 mL), and brine (20 mL), dried (MgSO4) and concentrated. Silica gel chromatography, loading with dichloromethane-hexanes (1:1) and eluting with 0 to 20% ethyl acetate in hexanes, gave 3,5-dichloro-2-(o-tolylamino)isonicotinonitrile as yellow solid (1.10 g, 76% yield). 1H NMR (400 MHz, CDCl3) δ ppm 8.18 (1H, s), 7.71 (1H, δ, J=7.78 Hz), 7.23-7.40 (2H, m), 7.01-7.13 (1H, m), 6.70-6.94 (1H, m), 2.29 (3H, s); MS (ES+) m/z: 278 (M+H); LC retention time: 3.68 min (analytical HPLC Method A).

Provenance & Evidence