Aluminum(III) Chloride → 6-Bromo-8-chloro-3,4-dihydroquinolin-2(1H)-one

HRID 1774842Notes

Reaction equation

HRID 1774842 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([NH:8][C:9](=[O:13])[CH2:10][CH2:11]Cl)=[C:4]([Cl:14])[CH:3]=1.[Cl-].[Al+3].[Cl-].[Cl-]>>[Br:1][C:2]1[CH:7]=[C:6]2[C:5](=[C:4]([Cl:14])[CH:3]=1)[NH:8][C:9](=[O:13])[CH2:10][CH2:11]2

Participants

3

Reactant 2

HCID 6451240Aluminum(III) ChlorideHCID 43346898N-(4-bromo-2-chlorophenyl)-3-chloropropanamide

Product 1

HCID 709797726-Bromo-8-chloro-3,4-dihydroquinolin-2(1H)-oneYield 27%

Conditions

Temperature
140 °C

Procedure

A flame-dried 500-mL flask equipped with a magnetic stirring bar was charged with N-(4-bromo-2-chloro-phenyl)-3-chloro-propionamide (29.7 g, 0.1 mol) and aluminium chloride (53.3 g, 0.4 mol). In a pre-heated oil bath, the flask was heated at 140° C. for 1 hour. After cooling to room temperature, the mixture was treated slowly with ice-water and extracted with EtOAc. The organic layer was washed with water and brine in sequence, dried over anhydrous Na2SO4, filtered, and concentrated in vacuo. The resulting residue was then purified by flash chromatography (silica gel, 30% ethyl acetate in hexane) to afford the title compound (7.0 g, 27%) as a white solid.

Workup

  1. customA flame-dried 500-mL flask equipped with a magnetic stirring bar
  2. temperatureAfter cooling to room temperature
  3. extractionextracted with EtOAc
  4. washThe organic layer was washed with water and brine in sequence
  5. dry with materialdried over anhydrous Na2SO4
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo
  8. customThe resulting residue was then purified by flash chromatography (silica gel, 30% ethyl acetate in hexane)

Sources & evidence

ORD record
ord-14841210e0a3403aac3467f75f6eeb56
Source dataset
uspto-grants-2016_02
Patent number
US09260408B2

Reaction notes

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