7-nitro-2-benzyloxy-2,3-dihydro-1H-isoindol-1-one → 7-Amino-2,3-dihydro-2-hydroxy-1H-isoindol-1-one

Participants

Reaction Steps

To a solution of 7-nitro-2-benzyloxy-2,3-dihydro-1H-isoindol-1-one (Compound 186B, 2.3 g, 1.2 mmol) in methanol (30 mL) in a Parr hydrogenation flask was added 200 mg of 5% Pd/C. The mixture was hydrogenated under 40 psi hydrogen pressure at room temperature overnight. The reaction mixture was filtered through a glass filter paper and the filtrate was concentrated to afford 1.2 g of the pure product (90%). 1H NMR (CDCl3, 600 MHz): δ=4.57 (s, 2 H), 5.04 (br, 2 H), 6.57 (d, J=7.8 Hz, 1 H) 6.65 (d, J=7.5 Hz, 1 H), 7.25 (dd, J=7.5, 7.8 Hz, 1 H), 10.2 (s, br, 1 H).

Provenance & Evidence