3-Cyanobenzoic acid → 3-Cyanobenzoyl chloride

Participants

Reaction Steps

Thionyl chloride (10 ml) and dimethylformamide (1 drop) were added to a solution of 3-cyanobenzoic acid (10 g) in dichloromethane (100 ml), and the mixture was refluxed far 3 hours. After the reaction, the solvent was evaporated under reduced pressure to give 3-cyanobenzoyl chloride. Then, the oil was dissolved in dichloromethane (25 ml), and the solution was dropwise added to a solution of 4-aminopyridine (5 g) and diisopropylethylamine (8.9 g) in dichloromethane (50 ml), which was followed by stirring at room temperature for 1 hour. The precipitated crystals were collected by filtration, and recrystallized from chloroform-methanol-ether to give 5.3 g of N-(4-pyridyl)-3-cyanobenzamide.

Provenance & Evidence