Acetic Acid → 7-Nitro-5-azaphenanthrene-1,10-dicarboxylic Anhydride

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8-Nitro-10-azaacephenanthrene (3.0 g, 24 mmol) was heated to 70° C. in acetic acid (100 mL) and sodium dichromate dihydrate (18.0 g, 60.4 mmol) was added. The reaction mixture was heated at reflux for 4 h and poured into ice/water. The precipitated solid was collected and dried in vacuo to obtain 1.64 g (34%) of a yellow solid. The crude material was heated at reflux in a mixture of acetic acid (25 mL) and acetic anhydride (5 mL) for 3 h. The mixture was filtered hot and the collected solid was dried in vacuo to give 0.90 g (17%) of a light brown solid: mp 290°-292° C.; MS m/e 312 (M+NH4+); 1H NMR (DMSO-d6, 300 MHz) δ 8.19 (t, J=4.0 Hz, 1H), 8.73 (d, J=7.3 Hz, 1H), 9.33 (s, 1H), 9.54 (d, J=8.0 Hz, 1H), 9.80 (d, J=2.5 Hz, 1H), 9.90 (d, J=2.0 Hz, 1H).

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