[CH3:1][O:2][C:3]1[CH:8]=[CH:7][CH:6]=[C:5]([NH2:9])[CH:4]=1.CCN([CH2:15][CH3:16])CC.C([CH:19]([CH2:23][C:24](Cl)=[O:25])[C:20](Cl)=[O:21])C.C1C[O:30]CC1>O.CCOC(C)=O>[CH3:1][O:2][C:3]1[CH:4]=[C:5]([NH:9][C:24](=[O:25])[CH2:23][CH2:19][C:20]([O:21][CH2:15][CH3:16])=[O:30])[CH:6]=[CH:7][CH:8]=1To a solution of m-anisidine (10 g, 81.3 mmol) in THF (240 mL) was added Et3N (22 mL, 217.8 mmol) followed by ethyl succinyl chloride (11.14 g, 67.9 mmol). The reaction mixture was stirred at ambient temperature for 15 minutes. The reaction was diluted with H2O and EtOAc and the organic layer was separated. The organic layers were washed with H2O, 10% HCl (aq), sat. NaHCO3 (aq) and brine, dried over MgSO4 and concentrated under reduced pressure to give the title compound as a pale yellow solid (17.5 g, 86%). 1H NMR (400 MHz, CDCl3) δ 7.62-7.56 (m, 1H), 7.32-7.28 (m, 1H), 7.19 (t, J=8.0 Hz, 1H), 6.95 (d, J=8.2 Hz, 1H), 6.65 (dd, J=8.2, 2.0 Hz, 1H), 4.17 (d, J=7.0 Hz, 2H), 3.80 (s, 3H), 2.81-2.70 (m, 2H), 2.70-2.60 (m, 2H), 1.26 (t, J=7.2 Hz, 3H). [M+H]=252.3.
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