Ethyl Acetate → HCID 58009999, compound

Participants

Reaction Steps

6-Chloro-4-(trifluoromethyl)nicotinic acid (1.0 g, 4.4 mmol, Oakwood) was dissolved in DCM (44 mL) to give a clear solution. SOCl2 (3.2 mL, 44 mmol) was added drop-wise and the reaction mixture was stirred at room temperature overnight and then at reflux for about 16 h. The mixture was concentrated under reduced pressure to give a yellow oil that was dissolved into EtOAc (10 mL). The solution was added drop-wise to a rapidly stirred mixture of EtOAc (20 mL) and concentrated aqueous NH4OH (22 mL, 580 mmol). The resulting cloudy mixture was stirred for about 2 h and separated. The aqueous layer was further extracted with EtOAc (30 mL). The combined organic extracts were washed with brine, dried over anhydrous Na2SO4, filtered, and concentrated under reduced pressure to give 6-chloro-4-(trifluoromethyl)nicotinamide (0.85 g, 85%) as off-white solid: LC/MS (Table 2, Method a) Rt=1.62 min; MS m/z: 223 (M+H)+.

Provenance & Evidence