Hydrochloric Acid → 4,4-Dimethyl-3,4-dihydroquinolin-2(1H)-one

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Reaction Conditions

Reaction Steps

To 3-methyl-but-2-enoic acid phenylamide (7.6 g, 43 mmol) in DCM (100 mL) was added AlCl3 (8.7 g, 65.2 mmol) and the mixture was stirred at 50° C. for 2 hrs. After cooling to rt, the mixture was treated with 1N HCl (50 mL) and extracted with DCM (30 mL×2). This solution was then washed with brine (50 mL×2) and dried over MgSO4. The filtrate was evaporated to afford 4,4-dimethyl-3,4-dihydro-1H-quinolin-2-one as a brown solid in quantitative yield (7.6 g). MS: 176.0 (M+H)+; tR=1.91 min (method 1).

Provenance & Evidence