Dichloromethane → 2-Chloro-N-methoxy-N-methylnicotinamide

Participants

Reaction Steps

[Step 1] 5.0 g of 2-chloronicotinic acid and 2.8 mL of thionyl chloride were dissolved in 60 mL of benzene and then refluxed while heating. Three hours later, after adding the reaction liquid to 50 mL of a separately prepared dichloromethane solution containing 4.6 g of N,O-dimethylhydroxyamine hydrochloride and 20 mL of pyridine while cooling with ice, the solution was stirred overnight at room temperature. Following completion of the reaction, the solution was concentrated under reduced pressure, and the resulting residue was purified by recrystallization (with a mixture of ethyl acetate and hexane) to obtain 5.1 g of 2-chloro-N-methoxy-N-methylnicotinamide in the form of pale yellow crystals (79%).

Provenance & Evidence