Nitric Acid → N-(4-cyclopentyl-2-nitrophenyl)acetamide

Participants

Reaction Steps

To a suspension of N-(4-cyclopentylphenyl)acetamide (Preparation 97, 18.5 g, 91.0 mmol) in acetic anhydride (148 mL, 1570 mmol) cooled in an ice/brine bath was added dropwise a solution of nitric acid (5.7 mL, 140 mmol) in acetic anhydride (40 mL, 400 mmol). After stirring for 4 hours, the reaction mixture was added water and extracted with methylene chloride (3×). The organic layers were combined, dried over anhydrous magnesium sulphate, filtered, and concentrated in vacuo. This provided product (19.48 g, 86%) as a brown oil that was used without further purification.

Provenance & Evidence