Ethyl Acetate → 2-(4-Chlorophenyl)-4-hydroxy-6,7-dimethoxyquinazoline

Reaction equation

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

Participants

Procedure

To a solution of 2-((4-chlorophenyl)carbonylamino)-4,5-dimethoxybenzamide (1.0 g, 2.99 mmol) in ethanol (10 mL) was added aqueous NaOH solution (15 mL) at rt for 10 min. The reaction mixture was refluxed for 10 min and allowed to rt. The mixture was poured into ice cold water and stirred for 10 min EtOAc (20 mL) was added to the solution and stirred for 5 min. The separated solid was filtered, washed with ice cold water and dried to the product as a white color solid (900 mg, 95%), mp>360° C. 1H NMR (400 MHz, DMSO-d6): δ 12.47 (1H, s), 8.19 (2H, d, J=8.6 Hz), 7.62 (2H, d, J=8.6 Hz), 7.50 (1H, s), 7.23 (1H, s), 3.94 (3H, s), 3.90 (3H, s); LC-MS (positive ion mode): m/z 317, 319 (M+H)±.