Acetic Acid → Ethyl 3-(2-chloro-5-nitropyridin-4-yl)-2-oxopropanoate

Participants

Reaction Steps

To a solution of potassium ethoxide (1.46 g, 17.4 mmol) in diethyl ether (80 mL) and ethanol (10 mL) under an argon atmosphere was added diethyl oxalate (2.4 mL, 17.4 mmol) and the mixture was stirred at rt for 30 min. A solution of 2-chloro-4-methyl-5-nitropyridine (3.0 g, 17.4 mmol) in diethyl ether (20 mL) was added resulting in the formation of a dark green precipitate. The reaction was stirred at rt for 15 h, cooled to 0° C., filtered and washed with cold diethyl ether to give a dark green solid. The solid was dissolved in water (200 mL) and acidified to pH 4 with acetic acid to give a precipitate. The solid was collected by filtration and dried to give the title compound. m/z (ES+)=273 [M+H]+.

Provenance & Evidence