Dimethylformamide → 2-Chloro-3-chloromethyl-pyridine

Participants

Reaction Steps

To a stirred solution of 2-chloronicotinic acid (500 mg, 3.17 mmol) in anhydrous dichloromethane (10 ml) was added dropwise oxalyl chloride (0.407 ml, 4.76 mmol) at a room temperature. A drop of anhydrous N,N-dimethylformamide was added and the reaction mixture stirred for 2 hours at a room temperature. Once the reaction was completed, intermediate product, i.e., 2-chloronicotinyl chloride was obtained with vacuum-concentration. Anhydrous dichloromethane (10 ml) was added, and then 3-anisidine (0.390 ml, 3.49 mmol) in anhydrous dichloromethane (5 ml) was added dropwise at 0° C. to a solution of the above mixture. Triethylamine (0.885 ml, 6.347 mmol) was added and the mixture was stirred for one hour at 0° C. Once the reaction was completed, water was added and the resultant mixture was extracted with dichloromethane. The separated organic layer was dried over anhydrous magnesium sulfate, and the solvent was concentrated under reduced pressure to obtain the title compound (970 mg, ivory oil).

Provenance & Evidence