2-amino-n-(4-bromophenyl)benzamide → 3-(4-bromophenyl)-2-(4-(2-hydroxyethoxy)-3-methylphenyl)quinazolin-4(3H)-one
Reaction equation
[CH3:1][C:2]1[CH:3]=[C:4]([CH:7]=[CH:8][C:9]=1[O:10][CH2:11][CH2:12][OH:13])[CH:5]=O.[NH2:14][C:15]1[CH:30]=[CH:29][CH:28]=[CH:27][C:16]=1[C:17]([NH:19][C:20]1[CH:25]=[CH:24][C:23]([Br:26])=[CH:22][CH:21]=1)=[O:18]>C(O)C>[Br:26][C:23]1[CH:24]=[CH:25][C:20]([N:19]2[C:17](=[O:18])[C:16]3[C:15](=[CH:30][CH:29]=[CH:28][CH:27]=3)[N:14]=[C:5]2[C:4]2[CH:7]=[CH:8][C:9]([O:10][CH2:11][CH2:12][OH:13])=[C:2]([CH3:1])[CH:3]=2)=[CH:21][CH:22]=1Participants
4
Procedure
To a solution of 3-methyl-4-hydroxyethoxy-benzaldehyde (0.38 g, 2.10 mmol) and 2-amino-N-(4-bromophenyl)benzamide (0.60 g, 2.10 mmol) in anhydrous ethanol (15 mL) was added anhydrous CuCl2 (0.85 g, 6.30 mmol). The reaction mixture was heated at reflux for 18 hours and then cooled to room temperature. Organic solvents were removed under reduced pressure, and the resulting residue was diluted with dichloromethane, washed with water, then brine, and dried over anhydrous magnesium sulfate. The solvent was removed under vacuum and the residual solid was purified by column chromatography (silica gel 230-400 mesh; 25-50% ethyl acetate in hexanes as eluent) to afford the title compound as a white solid. Yield: 0.21 g (22%). MP 92.0-93.0° C. 1H-NMR (400 MHz, CDCl3): δ 8.32 (d, J=8.4 Hz, 1H), 7.81 (dd, J=4.8 and 1.2 Hz, 2H), 7.45-7.54 (m, 3H), 7.23 (m, 1H), 7.00 (m, 3H), 6.63 (d, J=8.4 Hz and 1H), 4.05 (t, J=4.4 Hz, 2H), 3.97 (t, J=4.4 Hz, 2H), 2.15 (s, 3H). MS (ES+) m/z: 453.39, 451.37.