2-Naphthoic acid → 2-Naphthylamine

Participants

Reaction Conditions

Reaction Steps

Polyphosphoric acid (7.5 g) was added to a mixture of 2-naphthoic acid (600 mg, 3.48 mmol) and hydroxylamine hydrochloride (254 mg, 3.66 mmol) at room temperature and heated slowly to 160° C. The reaction mixture was stirred for 90 min and then allowed to cool to ambient temperature and quenched with crushed ice (50 g). The resultant solid was filtered and washed with water (2×20 mL). The combined filtrate and washings were basified with 10% potassium hydroxide solution (100 mL). The precipitated solid was filtered, washed with water (2×25 mL), petroleum ether (2×20 mL), diethyl ether (2×20 mL) and dried in vacuo to afford naphthalen-2-amine (165 mg, 34%) as a light pink solid.

Provenance & Evidence