Benzoyl chloride, 3-chloro- → HCID 67342733, compound

Participants

Reaction Steps

To a solution of 0.45 g (1.7 mmol) of 3′-amino-5′-chloro-3,4,5,6-tetrahydro-2H-[1,2′]bipyridinyl-4-carboxylic acid methyl ester in acetonitrile (20 mL) is added 0.23 mL (1.0 mmol) of 3-chlorobenzoyl chloride. The mixture is stirred at room temperature overnight then concentrated under reduced pressure and the residue is taken up in water and extracted with ethyl acetate. The combined organic phase is washed with a 10% aqueous solution of sodium hydroxide followed by brine then dried over anhydrous sodium sulfate and concentrated under reduced pressure. The residue is purified by flash silica gel chromatography to provide, after concentration of the eluent, a yellow oil. The oil is dissolved in methanol and upon standing a solid precipitates from solution. The material is collected by filtration and dried on the filter pad to provide 0.38 g (56%) of 5′-chloro-3′-(3-chloro-benzoylamino)-3,4,5,6-tetrahydro-2H-[1,2′]bipyridinyl-4-carboxylic acid methyl ester as a white solid.

Provenance & Evidence