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

HRID 1774833Notes

Reaction equation

HRID 1774833 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 hours. After cooling to room temperature, the reaction mixture was treated slowly with ice-water, then extracted with EtOAc. The organic layer was washed with water and brine in sequence and dried over anhydrous Na2SO4. After evaporation of the solvent, the residue was purified by recrystallization from EtOAc (2 mL) which gave title compound (0.44 g, 50%) 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 hours
  3. extractionextracted with EtOAc
  4. washThe organic layer was washed with water and brine in sequence
  5. dry with materialdried over anhydrous Na2SO4
  6. customAfter evaporation of the solvent
  7. customthe residue was purified by recrystallization from EtOAc (2 mL) which

Sources & evidence

ORD record
ord-21fb40fc4a674337b121db420117bb32
Source dataset
uspto-grants-2016_02
Patent number
US09260408B2

Reaction notes

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