HCID 532094, compound → 3,4-Dihydro-6-methoxy-4,4-dimethyl-2(1H)-quinolinone

Participants

Reaction Steps

A solution of 3-methyl-N-[4-(methyloxy)phenyl]-2-butenamide (5.8 g, 28 mmol) in dichloromethane (250 mL) was treated with aluminum trichloride (13 g, 97 mmol, Aldrich). The mixture was refluxed for 7 h, cooled, and then poured over ice. The organic layer was separated, dried over magnesium sulfate, filtered, and concentrated to give 4,4-dimethyl-6-(methyloxy)-3,4-dihydro-2(1H)-quinolinone (4.5 g, 77%). 1H NMR (400 MHz, DMSO-d6) δppm 1.20 (s, 6 H), 2.29 (s, 2 H), 3.71 (s, 3 H), 6.72-6.81 (m, 2 H), 6.83 (d, J=2.6 Hz, 1 H), 9.97 (s, 1 H).

Provenance & Evidence