3-(Trifluoromethyl)benzylamine → N-(3-(trifluoromethyl)benzyl)-2-chloroisonicotinamide

Participants

Reaction Conditions

Reaction Steps

Into a 500-mL round bottom flask, was placed a solution of 2-chloroisonicotinic acid (18 g, 113.92 mmol, 2.00 equiv) in dichloromethane (200 mL), 3-(trifluoromethyl)benzylamine (10 g, 57.14 mmol, 1.00 equiv), EDC.HCl (22 g, 115.18 mmol, 2.00 equiv), and 4-dimethylaminopyridine (14 g, 114.75 mmol, 2.00 equiv). The resulting solution was stirred for 3 h at 25° C. The resulting solution was diluted with 500 mL of dichloromethane. The resulting mixture was washed with 2×50 mL of aqueous NH4Cl, 1×50 mL of 10% sodium bicarbonate, and 1×50 mL of brine. The mixture was dried over anhydrous sodium sulfate and concentrated under vacuum. The residue was applied onto a silica gel column and eluted with petroleum ether/ethyl acetate (5:1). The product was obtained as 11.8 g (63%) of a white solid.

Provenance & Evidence