N-hydroxy-2-methoxy-5-nitrobenzamide → 2-methoxy-5-amino-N-hydroxybenzamide

Participants

Reaction Steps

N-Hydroxy-2-methoxy-5-nitrobenzamide (approx. 47.39 mmol) was taken up in IMS (500 ml) and 10% Pd on C (50% wet) (1 g) was added. The mixture was hydrogenated at 50 psi for 1.5 hr, then filtered through celite, and the celite washed with 2M NaOH (200 ml). The MeOH was removed in vacuo and the resulting aqueous residue washed with MTBE (100 ml). The pH of the aqueous was lowered to 7 by the careful addition of concentrated HCl, and the resulting precipitated solid collected by filtration, washed with H2O, then MTBE and dried under high vacuum overnight to give 5.33 g of the title compound (62%) as a light brown solid.

Provenance & Evidence