[I:1][C:2]1[CH:3]=[C:4]2[C:9](=[O:10])[O:8][C:6](=O)[C:5]2=[CH:11][CH:12]=1.[NH2:13][C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1.N1C=CC=CC=1.C(OC(=O)C)(=O)C>CO.CC(N(C)C)=O>[I:1][C:2]1[CH:3]=[C:4]2[C:9](=[O:10])[N:13]([C:14]3[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=3)[C:6](=[O:8])[C:5]2=[CH:11][CH:12]=1As described above, 4-iodophthalic anhydride (2.0 g, 7.3 mmol), aniline (665 μL, 7.3 mmol), pyridine (2.1 mL, 25.5 mmol) and DMAc (10 mL) were heated at 80° C. for 2 hours, followed by continued heating in the presence of acetic anhydride (2.75 mL, 29.2 mmol) for 16 hours. MeOH (5 mL) was added to the warm solution which was then cooled to room temperature. The crystalline solid was removed by filtration, washed with MeOH and dried in vacuo to give 1.96 g (77%) product. The filtrate was concentrated and cooled to 0° C. to afford another 300 mg (11%) product. Total yield 88% mp 178°-179° C., 1H NMR (CDCl3) δ8.27 (d, J=1.0 Hz, 1), 8.13 (dd, J=7.5, 1.0 Hz, 1), 7.65 (d, J=7.9 Hz, 1), 7.49 (m, 2), 7.40 (m, 3). 13C NMR (CDCl3) {1H} δ166.6, 165.7, 143.3, 133.1, 132.8, 131.5, 131.0, 129.1, 128.2, 126.4, 124.9, 101.1. Combustion analysis calculated for C14H8INO2 : C, 48.16; H, 2.31; N, 4.01. Found: C, 47.81; H, 2.39; N, 3.95.
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