2-Chloro-5-nitropyridine → Dibenzyl 5-nitro-2-pyridylmalonate

Participants

Reaction Conditions

Reaction Steps

A solution of potassium tert-butoxide in dimethylsulfoxide was treated with dibenzyl malonate. This mixture was stirred at 95° C. for 10 min. At this time, the reaction was treated with a solution of 2-chloro-5-nitropyridine. The resulting mixture was stirred at 95° C. for 1.5 h. At this time, the reaction mixture was poured into ice/water and extracted with ethyl acetate. The organics were washed with a saturated aqueous sodium chloride solution, dried over sodium sulfate, filtered, and concentrated in vacuo. Flash chromatography (Merck Silica gel 60, 230–400 mesh, 20/80 ethyl acetate/hexanes) afforded 2-(5-nitro-pyridin-2-yl)-malonic acid dibenzyl ester (45%) as a bright yellow solid; LRMS for C22H18N2O6 (M−H)+ at m/z=405.

Provenance & Evidence