Diethyl Oxalate → potassium (1Z)-1-[2-(dibenzylamino)-3-nitropyridin-4-yl]-3-ethoxy-3-oxoprop-1-en-2-olate

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Reaction Steps

A slurry of potassium ethoxide (391 mg, 4.64 mmol) in diethyl ether (4 mL) under N2 was cooled to 0° C. under vigorous stirring. Diethyl oxalate (0.63 mL, 4.65 mmol) was added, and the mixture was stirred for 5 min. A solution of 2-(dibenzylamino)-4-methyl-3-nitropyridine (1.52 g, 4.56 mmol) in diethyl ether (3 mL) was added, and the mixture was stirred for 16 h while slowly warming to room temperature, during which time a precipitate formed. The solid was collected on a sintered glass frit and rinsed several times with additional diethyl ether. The solid was transferred to a vial and dried under vacuum at 30° C. for 2 h to provide potassium (1Z)-1-[2-(dibenzylamino)-3-nitropyridin-4-yl]-3-ethoxy-3-oxoprop-1-en-2-olate (1.63 g, 3.46 mmol, 76%) as a light orange solid. This product was immediately used without purification or identification.

Provenance & Evidence