1-(4-Nitro-1-oxoisoindolin-2-yl)propane-1,3-dicarboxylic acid dibenzyl ester → 2-(4-Amino-1-oxoisoindolin-2-yl)pentanedioic acid

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Reaction Steps

A mixture of 1-(4-nitro-1-oxoisoindolin-2-yl)propane-1,3-dicarboxylic acid dibenzyl ester (2.6 g, 5.3 mmol), 10%Pd/C (0.26 g) and methanol (50 mL) is hydrogenated at 50 psi of hydrogen for 6 hours. The mixture is filtered through celite and the celite pad is washed with methanol (50 mL). The filtrate is concentrated in vacuo to give 1-(4-amino-1-oxoisoindolin-2-yl)propane-1,3-dicarboxylic acid (1.2 g, 81%); mp 183-185° C.; 1H NMR (DMSO-d6) δ7.17 (t, J=7.6 Hz, 1H), 6.89 (d, J=7.3 Hz, 1H), 6.79 (d, J=7.8 Hz, 1H), 5.50 (b, 2H), 4.82-4.77 (m, 1H), 4.23 (s, 2H), 2.31-1.98 (m, 4H); 13C NMR (DMSO-d6) δ173.46, 172.28, 168.98, 143.58, 132.21, 128.73, 125.65, 116.24, 110.34, 52.83, 45.19, 30.32, 24.42; Anal. Calcd. For C13H14N2O5; C, 56.11; H, 5.07; N, 10.07. Found: C, 55.95; H, 5.37; N, 9.73.

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