Under stirring conditions, m-aminoanisole (26 mL, 0.23 mol) was slowly added dropwise to acetic acid (2.6 mL), followed by the slow addition of 4-methyl-3-penten-2-one (27 mL, 0.23 mol). The reaction mixture was stirred at room temperature overnight and then concentrated hydrobromic acid (50 mL) was added. After continued stirring for 1 h, the precipitate was collected by filtration and washed with acetone. The resulting solid was dissolved in water (100 mL) and the pH was adjusted to 7 with 10 N aqueous sodium hydroxide.The aqueous phase was extracted with chloroform (3 x 50 mL), the organic phases were combined and dried over anhydrous sodium sulfate. After filtration to remove sodium sulfate, the filtrate was concentrated in vacuum to give the crude product. The crude product was recrystallized from hexane to give 7-methoxy-2,2,4-trimethyl-1,2-dihydroquinoline (15.5 g, 33% yield) as a pale yellow solid.
