Ethyl Acetate → 5-Chloro-1-methyl-3,4-dihydroquinolin-2(1H)-one

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Reaction Steps

3-(2-Bromo-6-chlorophenyl)-N-methylpropanamide (Example 1g), 2.98 g, 10.8 mmol), palladium acetate (0.12 g, 0.54 mmol), Pd2(dba)3 (0.020 g, 0.02 mmol), racemic 2,2′-bis(diphenylphosphino)-1,1′-binaphthyl (0.671 g, 1.08 mmol) and cesium carbonate (4.92 g, 15.1 mmol) in toluene (30 mL) and 1,4-dioxane (45 mL) were heated to +95° C. under argon for 6 h. The mixture was allowed to cool to rt. 100 mL of ethyl acetate was added and the mixture was filtered through a pad of Celite. The filtrate was collected and the solvent was removed by rotary evaporation. The crude product was added to a silica gel column and was eluted with 0-2% methanol in dichloromethane. The collected fractions were combined and the solvent was removed by rotary evaporation to give the title compound. Yield: 1.50 g, 71%. 1H NMR (500 MHz, CDCl3) δ ppm 2.66 (dd, 2H) 3.02-3.09 (m, 2H) 3.36 (s, 3H) 6.91 (d, 1H) 7.08-7.12 (m, 1H) 7.17-7.22 (m, 1H). MS m/z 196.6 [M+H]+

Provenance & Evidence