Aluminum(III) Chloride → 7-Bromo-4,4-dimethyl-3,4-dihydroquinolin-2(1H)-one
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]1Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
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.