Triethylamine → Ethyl 4-[(2-chloro-5,6-dimethyl-3-nitropyridin-4-yl)amino]butyrate

Participants

Reaction Steps

Under a nitrogen atmosphere, triethylamine (47 mL, 340 mmol) was added to a solution of 2,4-dichloro-5,6-dimethyl-3-nitropyridine (30.0 g, 136 mmol) and ethyl 4-aminobutyrate hydrochloride (32 g, 190 mmol) in DMF (500 mL), and the reaction was stirred overnight. The solvent was removed under reduced pressure, and the residue was partitioned between chloroform (500 mL), water (25 mL), and brine (25 mL). The organic layer was separated and washed with water:brine (1:1, 3×50 mL), dried over magnesium sulfate, filtered, and concentrated under reduced pressure. The resulting orange solid was recrystallized from ethyl acetate:hexanes and dried under high vacuum to provide 21.5 g of ethyl 4-[(2-chloro-5,6-dimethyl-3-nitropyridin-4-yl)amino]butanoate.

Provenance & Evidence