Acetic Acid → 4-(6,7-Dimethoxyquinazolin-4-yloxy)benzene-1,2-diamine

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[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][C:12]=1[O:13][CH3:14])[N:9]=[CH:8][N:7]=[C:6]2[O:15][C:16]1[CH:21]=[CH:20][C:19]([NH2:22])=[C:18]([N+:23]([O-])=O)[CH:17]=1.C(O)(=O)C>CCO.[Pd]>[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][C:12]=1[O:13][CH3:14])[N:9]=[CH:8][N:7]=[C:6]2[O:15][C:16]1[CH:17]=[C:18]([NH2:23])[C:19]([NH2:22])=[CH:20][CH:21]=1

참가 물질

실험 절차

4-(6,7-Dimethoxyquinazolin-4-yloxy)-2-nitro-phenylamine (Step A, 1 g, 2.9 mmol) was dissolved in EtOH (200 mL) and glacial acetic acid (10 mL) and placed under nitrogen. Pd/C was added, the reaction mixture blanketed with H2, the mixture was shaken under H2 for 18 h at 55 psi. The catalyst was removed by filtration through Celite® and the solution was concentrated in vacuo. The residue was dissolved in MeOH/H2O and NH4OH was added to adjust to PH 10, and the solvent evaporated. Purification of the residue by column chromatography using a gradient of 0-100% of a 90:10:1 (CH2Cl2:MeOH: NH4OH) afforded the title compound as a orange solid. MS(MH+)=N/A; Calc'd 312.32 for C16H16N4O3.