Thionyl Chloride → HCID 59652740, compound

Participants

Reaction Steps

To a solution of 5-amino-2-chlorobenzoic acid (1.71 g, 10 mmol) and TEA (6.96 mL, 50 mmol) in THF (50 mL) was added nicotinoyl chloride hydrochloride (1.78 g, 10 mmol) solid portion-wise. After 1 h stirring at room temperature, product was isolated through filtration as a white solid. The solid was washed with water and dried (1.85 g, 67%). The solid, 2-chloro-5-(nicotinamido)benzoic acid (1.0 g, 3.62 mmol) was suspended in dichloromethane (50 mL) and treated with thionyl chloride (1.57 mL, 36.2 mmol) at reflux for 6 hr. The reaction mixture was evaporated, and the residue was dissolved in hexane-ethyl acetate mixture (100 mL, 6:4) and quickly filtered through a short silica plug. On evaporation of solvent, the title compound was obtained as a white solid (873 mg, 82%).

Provenance & Evidence