2-Butenamide, N-(4-bromophenyl)-3-methyl- → 6-bromo-4,4-dimethyl-3,4-dihydroquinolin-2(1H)-one

Temperature

130 °C

To 6.7 g (26.02 mmol) of molten N-(4-bromophenyl)3,3-dimethylacrylamide (heated to 135° C.) was added 4.15 g (31.09) of aluminum chloride over 25 minutes. The reaction mixture was stirred at 130° C. for 16 hours and then treated with a further 1 g of aluminum chloride. The reaction mixture was heated at 130° C. for a further 9 hours and then cooled to room temperature. The reaction was then quenched by the slow addition of 100 ml of ice cold water with slight warming of flask to facilitate mixing. The mixture was extracted with 1×100 ml and 4×50 ml of ether. The organic extracts were combined and washed with 25 ml of saturated NaCl solution and then dried (MgSO4). The solvent was removed in vacuo and the residue purified by flash chromatography (silica; 30% ethyl acetate in hexanes) to give the title compound as a pale yellow solid.

1. temperatureThe reaction mixture was heated at 130° C. for a further 9 hours
2. temperaturecooled to room temperature
3. customThe reaction was then quenched by the slow addition of 100 ml of ice cold water
4. temperaturewith slight warming of flask
5. additionto facilitate mixing
6. extractionThe mixture was extracted with 1×100 ml and 4×50 ml of ether
7. washwashed with 25 ml of saturated NaCl solution
8. dry with materialdried (MgSO4)
9. customThe solvent was removed in vacuo
10. customthe residue purified by flash chromatography (silica; 30% ethyl acetate in hexanes)

ORD record

ord-020457bb2e934523b5acf665fdce07dd

Source dataset

uspto-grants-1994_10

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US05354752