Picolinic acid → 4-chloro-N-(2-(dimethylamino)ethyl)picolinamide

Participants

Reaction Conditions

Reaction Steps

To a solution of thionyl chloride (7.4 mL, 101 mmol) in DMF was added pyridine-2-carboxylic acid (2.5 g, 20.3 mmol). The reaction mixture was heated at 95° C. for 12 h and then concentrated. The residue was redissolved in DMF (7 mL) and N,N-dimethylethane-1,2-diamine (11 mL, 101.5 mmol) was added. After stirring for 15 min, the mixture was concentrated and the residue was purified by column chromatography (0-10% methanol/dichloromethane) to yield 2.11 g of the title compound (46%). LCMS: (FA) ES+ 227.9 (M+1)

Provenance & Evidence