2-Aminophenol → 4-fluoro-N-(2-hydroxyphenyl)-3-nitrobenzanilide

Participants

Reaction Steps

To a solution of 4-fluoro-3-nitrobenzoic acid (2.00 g, 10.8 mmol) in chloroform (40 mL) was added 2-aminophenol (1.18 g, 10.8 mmol), 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride (2.17 g, 11.3 mmol), and triethylamine (1.15 g, 11.3 mmol), and this was stirred at room temperature for 2.5 hours. After the reaction was complete, this was diluted by adding ethyl acetate, and this was washed with water, 1N hydrochloric acid, and saturated aqueous sodium hydrogen carbonate. The organic layer obtained was dried over anhydrous sodium sulfate, after which it was filtered and concentrated to yield the title compound (2.02 g, 68% yield) as orange crystals.

Provenance & Evidence