4-Bromoaniline → 6-Bromoquinolin-2(1H)-one
Reaction equation
[Br:1][C:2]1[CH:8]=[CH:7][C:5]([NH2:6])=[CH:4][CH:3]=1.[C:9]([Cl:19])(=[O:18])[CH:10]=[CH:11]C1C=CC=CC=1>>[Cl:19][C:9]1[CH:10]=[CH:11][C:7]2[C:5](=[CH:4][CH:3]=[C:2]([Br:1])[CH:8]=2)[N:6]=1.[Br:1][C:2]1[CH:8]=[C:7]2[C:5](=[CH:4][CH:3]=1)[NH:6][C:9](=[O:18])[CH:10]=[CH:11]2Participants
4
Procedure
The title compound is prepared from 4-bromoaniline and cinnamoyl chloride according to the procedure described in J. Chem. Soc., Perkin Trans. I, 1972, 1648. The crude 6-bromo-1H-quinolin-2-one intermediate obtained is triturated in Et2O/hexanes and filtered to give a beige solid which is used directly in the chlorination step. The crude product is recrystallized in MeOH to afford the title compound as a beige solid.
Sources & evidence
- ORD record
- ord-d45dd22efe384d6e8d41b31969ccab08