Aluminum(III) Chloride → 6-bromo-4,4-dimethyl-3,4-dihydroquinolin-2(1H)-one

HRID 1608944Notes

Reaction equation

HRID 1608944 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([N-:8][C:9](=[O:14])[CH:10]=[C:11]([CH3:13])[CH3:12])=[CH:4][CH:3]=1.[Cl-].[Al+3].[Cl-].[Cl-]>>[CH3:13][C:11]1([CH3:12])[C:4]2[C:5](=[CH:6][CH:7]=[C:2]([Br:1])[CH:3]=2)[NH:8][C:9](=[O:14])[CH2:10]1

Participants

3

Reactant 2

HCID 6451240Aluminum(III) Chloride2×HCID 178447218HCID 178447218, compound

Product 1

HCID 107295896-bromo-4,4-dimethyl-3,4-dihydroquinolin-2(1H)-one

Conditions

Temperature
130 °C

Procedure

To 1.0 g (3.9 mmol) of (4-bromophenyl) 3,3-dimethylacryloylamide heated to 130 degrees C. was added 0.526 g (3.94 mmol) of aluminum chloride over a period of 30 minutes. The reaction mixture was heated for an additional 30 minutes. The mixture was treated again with 0.079 g (0.592 mmol) of aluminum chloride and heated at 130 degrees C. for 1 hour and 40 minutes. The reaction mixture was extracted with 20 ml ether and the combined organics washed with 20 ml water, 20 ml brine and dried (MgSO4). Solvent was removed in-vacuo and the residue purified by flash chromatography (SiO2 ; 20% ethyl acetate in hexanes) to give the title compound as a light yellow solid.

Workup

  1. temperatureThe reaction mixture was heated for an additional 30 minutes
  2. custom40 minutes
  3. extractionThe reaction mixture was extracted with 20 ml ether
  4. washthe combined organics washed with 20 ml water, 20 ml brine
  5. dry with materialdried (MgSO4)
  6. customSolvent was removed in-vacuo
  7. customthe residue purified by flash chromatography (SiO2 ; 20% ethyl acetate in hexanes)

Sources & evidence

ORD record
ord-5fc60457e7ad42f2a37fa17e0ea78b97
Source dataset
uspto-grants-1995_03
Patent number
US05399561

Reaction notes

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