2-Methyl-7-nitro-2,3-dihydro-1H-isoindol-1-one → 7-Amino-2-methyl-2,3-dihydro-1H-isoindol-1-one

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Reaction Steps

A solution of 2-methyl-7-nitro-2,3-dihydro-1H-isoindol-1-one (Compound 17F, 6.09 g, 31 mmol) in DCM:ethanol (8:2) was hydrogenated under 40 psi of H2 in the presence of 5% Pd/C (500 mg) until cessation of H2 uptake. The reaction mixture was filtered, and the filtrate dried (Na2SO4) and concentrated in vacuo to afford 4.45 g of 7-amino-2-methyl-2,3-dihydro-1H-isoindol-1-one (yield: 73%). 1H NMR (CDCl3, 400 MHz): δ 3.11 (s, 3H), 4.27 (s, 2H), 5.19 (bs, 2H), 5.5 (d, 1H, J=7.8 Hz), 6.71 (d, 1H, J=7.2 Hz).

Provenance & Evidence