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

HRID 52445Notes

Reaction equation

HRID 52445 reaction equation
[Al+3].[Cl-].[Cl-].[Cl-].[CH3:5][C:6]([CH3:18])=[CH:7][C:8]([NH:10][C:11]1[CH:16]=[CH:15][CH:14]=[C:13]([Br:17])[CH:12]=1)=[O:9]>C(Cl)Cl>[CH3:5][C:6]1([CH3:18])[C:16]2[C:11](=[CH:12][C:13]([Br:17])=[CH:14][CH:15]=2)[NH:10][C:8](=[O:9])[CH2:7]1

Participants

4

Reactant 2

HCID 6451240Aluminum(III) ChlorideHCID 19177475N-3,3-Dimethylacryloyl-3-bromoaniline2×

Product 1

HCID 199637077-Bromo-4,4-dimethyl-3,4-dihydroquinolin-2(1H)-one

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

Into a 500 ml round-buttom flask was placed 13.52 g (101 mmol) of AlCl3 under nitrogen purge and kept at 0° C. Thereafter, 22.41 g of N-3,3-dimethylacryloyl-3-bromoaniline (Compound 17) in 350 ml CH2Cl2 was slowly added by syringe. The reaction mixture was stirred at 0° C. for 72 h, and thereafter slowly quenched with small chunks of ice-cubes and finally with water. The aqueous layer was washed with CH2Cl2 and the organic layer was dried over Na2SO4. The solvent was evaporated and the residue purified by recrystallization from EtOAc-hexane to give the title compound as off-white solids.

Workup

  1. customInto a 500 ml round-buttom flask was placed
  2. customkept at 0° C
  3. customslowly quenched with small chunks of ice-cubes and finally with water
  4. washThe aqueous layer was washed with CH2Cl2
  5. dry with materialthe organic layer was dried over Na2SO4
  6. customThe solvent was evaporated
  7. customthe residue purified by recrystallization from EtOAc-hexane

Sources & evidence

ORD record
ord-1062b5d1f0f24b1f95b2e920563ab6f5
Source dataset
uspto-grants-1997_04
Patent number
US05616712

Reaction notes

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