Acetamidomalonic acid diethyl ester → Diethyl acetamido[(pyridin-3-yl)methyl]propanedioate

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Reaction Steps

48 g of diethyl acetamidomalonate are added to 11 g of a solution of sodium in 300 ml of EtOH, and then, while heating under reflux, 36 g of 3-chloromethylpyridine hydrochloride are added and the mixture is kept under reflux for 5 h. The EtOH is evaporated off, the residue is taken up with water, the mixture is extracted and the extract is dried, concentrated and chromatographed on silica. Elution with a CH2Cl2 /AcOEt mixture, 60/40 by volume, gives 23 g of the expected compound.

Provenance & Evidence