2-Chloro-N-phenyl-isonicotinamide

65287-34-5

62-53-3

80194-83-8

General procedure for the synthesis of 2-chloro-N-phenylisonicotinamide: 2-chloroisonicotinoyl chloride (10 g, 56.8 mmol) was dissolved in 1,2-dichloroethane (100 mL) and cooled to 0 °C. A mixed solution of aniline (5.70 mL, 62.5 mmol) and N,N-diisopropylethylamine (DIPEA, 10.2 mL, 59.6 mmol) in 1,2-dichloroethane (10 mL) was added slowly over about 1 hour. The reaction mixture was stirred at 0 °C for 1 h, then warmed up to 95 °C and kept for 1 h. The reaction was carried out at 0 °C. Upon completion of the reaction, it was cooled to room temperature, the reaction was quenched by the addition of water (30 mL) and the mixture was filtered. The filtrate was extracted with dichloromethane (200 mL) and the organic phases were combined. The organic phase was dried with anhydrous magnesium sulfate, filtered and concentrated under reduced pressure. The residue was recrystallized with methanol/water (1:10, 110 mL) to afford the target product 2-chloro-N-phenylisonicotinamide (12.12 g, 92% yield).LC-MS analysis: retention time (RT) = 0.87 min; electrospray ionization mass spectrometry (ES+) = 233.1.