Sodium → ethyl beta-[N-(2-dimethylaminoethyl)-2-oxo-4-pyridyl]propionate

Participants

Reaction Steps

To a cooled solution of sodium (7.50 g) in ethanol (150 ml) was added a solution of ethyl β-(2-hydroxy-4-pyridyl)propionate (29.07 g) in ethanol (175 ml). After the solution was stirred for 40 minutes a solution of dimethylaminoethyl chloride hydrochloride (21.78 g) in ethanol (175 ml) was added and the reaction mixture was stirred under reflux for 6 hours and then was allowed to cool overnight. The reaction mixture was filtered and evaporated under reduced pressure to remove most of the solvent. Water (150 ml) was added and the solution was extracted with ethyl acetate (3×200 ml). The combined ethyl acetate extracts were dried over MgSO4 and evaporated under reduced pressure to yield an oil which was subjected to medium pressure column chromatography (using Kieselgel 60 silica gel 70-230 mesh-pre column and 230-400 mesh-main column) with gradient elution (dichloromethane→10% methanolic dichloromethane). The fractions containing the desired product were combined and evaporated under reduced pressure to yield ethyl β-[N-(2 -dimethylaminoethyl)-2-oxo-4-pyridyl]propionate (25.43 g) as an oil.

Provenance & Evidence