3-Nitrophthalic anhydride → 1-(4-Nitro-1,3-dioxoisoindolin-2-yl)propane-1,3-dicarboxylic acid

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A mixture of 3-nitrophthalic anhydride (1.5 g, 7.77 mmol) and L-glutamic acid (1.2 g, 7.77 mmol) in DMF (15 mL) is heated at 85° C. for 6 hours. The mixture is concentrated in vacuo and the residue is purified by chromatography (silica gel, CH2Cl2:CH3OH 95:5) to give 1-(4-nitro-1,3-dioxoisoindolin-2-yl)propane-1,3-dicarboxylic acid (1.51 g, 60%); 1H NMR (DMSO-d6) δ8.32 (d, J=7.9 Hz, 1H), 8.21 (d, J=7.3 Hz, 1H), 8.10 (t, J=7.8 Hz, 1H), 4.88-4.82 (dd, J=3.0 and 10.0 Hz, 1H), 2.35-2.20 (m, 4H).

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