3-Amino-2-naphthoic acid → (3-Aminonaphthalen-2-yl)methanol

Participants

Reaction Steps

To a solution of 3-amino-2-naphthoic acid (2 g, 10.7 mmol) in THF (11 mL) at 0° C. is added a 1 M solution of borane-tetrahydrofuran complex (27 mL) dropwise over 15 min. The mixture is allowed to warm to ambient temperature and stirred for 6 h. The excess borane-tetrahydrofuran complex is quenched by adding methanol at 0° C., and the solvent evaporated to obtain a yellow solid. The solid is washed with water, EtOAc and then dried under high vacuum to give (3-aminonaphthalen-2-yl)-methanol.

Provenance & Evidence