4-Bromoaniline → 6-Bromoquinolin-2(1H)-one

HRID 2782

Reaction equation

HRID 2782 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]2

Participants

4

Reactant 2

HCID 78074-BromoanilineHCID 660233-Phenylprop-2-enoyl chloride

Product 2

HCID 123789436-Bromoquinolin-2(1H)-oneHCID 128940866-Bromo-2-chloroquinoline

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
Source dataset
uspto-grants-1998_03
Patent number
US05731315

Linked notes

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