Aluminum(III) Chloride → 6-Bromo-7-chloro-3,4-dihydroquinolin-2(1H)-one

HRID 530340Notes

Reaction equation

HRID 530340 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([NH:8][C:9](=[O:13])[CH2:10][CH2:11]Cl)=[CH:4][C:3]=1[Cl:14].[Cl-].[Al+3].[Cl-].[Cl-]>>[Br:1][C:2]1[CH:7]=[C:6]2[C:5](=[CH:4][C:3]=1[Cl:14])[NH:8][C:9](=[O:13])[CH2:10][CH2:11]2

Participants

3

Reactant 2

HCID 6451240Aluminum(III) ChlorideHCID 86679184N-(4-bromo-3-chloro-phenyl)-3-chloro-propionamide

Product 1

HCID 709793626-Bromo-7-chloro-3,4-dihydroquinolin-2(1H)-oneYield 50.3%

Procedure

A flame-dried 50-mL flask equipped with a magnetic stirring bar was charged with N-(4-bromo-3-chloro-phenyl)-3-chloro-propionamide (1.0 g, 3.36 mmol) and aluminium chloride (0.67 g, 5.04 mmol). In a pre-heated oil bath, the flask was heated at 135˜140° C. for 2 hr. After cooling to room temperature, the reaction mixture was treated with ice-water slowly, and extracted with EtOAc. The organic layer was washed with water and brine in sequence, dried over anhy. Na2SO4. After evaporation of the solvent, the residue was purified by recrystallization in EtOAc (2 mL) and gave title compound (0.44 g, 50% yield) as a solid. MS: 260.0 (M+H)+.

Workup

  1. customA flame-dried 50-mL flask equipped with a magnetic stirring bar
  2. temperatureIn a pre-heated oil bath, the flask was heated at 135˜140° C. for 2 hr
  3. extractionextracted with EtOAc
  4. washThe organic layer was washed with water and brine in sequence
  5. customdried over anhy
  6. customAfter evaporation of the solvent
  7. customthe residue was purified by recrystallization in EtOAc (2 mL)

Sources & evidence

ORD record
ord-1991a92e488540498ca369e2a41e59f7
Source dataset
uspto-grants-2016_05
Patent number
US09353081B2

Reaction notes

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