(3-Nitrophenoxy)acetic acid → (3-Aminophenoxy)acetic acid

Participants

Reaction Steps

To a 2 L pressure vessel was added 3-nitrophenoxyacetic acid 1 (21.7 g, 110 mmol, 1.0 eq.) and methanol (600 mL). The resulting solution was purged with N2 for 5 min. 10% Pd/C (900 mg) was added to the solution and the vessel was placed on a Parr hydrogenator at 50 psi for 3 h. After removal from the Parr apparatus, the reaction mixture was gray in color, indicating the precipitation of product. DMF (400 mL) was added and was stirred until it was evident that the precipitated product had dissolved in the solvent phase. The Pd/C was removed by filtration and the filtrate was concentrated under high vacuum to yield a dark brown solid (14 g, 76%). LC/MSD (HP Series 1100 MSD) MS (ES+) m/z 168.0 (M+H)+1 1H-NMR, Varian 400 MHz (DMSO-d6) δ 7.93 (s, 1H), 6.86 (t, 1H), 6.14-5.99 (m, 3H), 4.50 (s, 2H) ppm.

Provenance & Evidence