Aluminum(III) Chloride → 4,4-Dimethyl-3,4-dihydroquinolin-2(1H)-one

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Reaction Steps

To a 500 mL round bottom flask containing AlCl3 (5.22 g, 0.039 mol) was added dry CH2Cl2 (40 mL). Then a solution of N-(3,3-dimethylacryloyl) aniline (Compound 37, 4.45 g, 0.025 mol) in CH2Cl2 (50 mL) was added slowly. The reaction mixture was stirred at room temperature for overnight followed by the addition of ice-cubes. This mixture was extracted with ethyl acetate (2×20 mL). The combined organic layers were washed with NaCl (sat.), dried over MgSO4 and concentrated to give a brownish oil. Purification of this oil by column chromatography (10% ethyl acetate in hexane) gave the title compound as a light yellow solid (2.31 g, 52%). 1H NMR d 1.34 (s, 6H), 2.51 (s, 2H), 6.85 (d, J=7.8 Hz, 1H), 7.29 (d, J=7.6 Hz, 1H), 7.03-7.08 (m, 1H), 7.16-7.23 (m, 1H), 9.01 (b, 1H).

Provenance & Evidence