Methyl iodide → 7-Methoxy-3,4-dihydroquinolin-2(1H)-one

Participants

Reaction Steps

To a solution of 7-hydroxy-3,4-dihydro-quinolin-2(1H)-one (1.50 g) in N,N-dimethylformamide (10 ml), potassium carbonate (1.85 g) and methyl iodide (0.63 ml) were added and stirred overnight at room temperature. Insoluble materials were filtered off and the filtrate was concentrated. The resulting residue was diluted with ethyl acetate and then washed sequentially with water, saturated aqueous sodium thiosulfate:brine (1:1) and brine, followed by distilling off the solvent under reduced pressure. The resulting residue was diluted with n-hexane, and the crystal was collected by filtration to give 7-methoxy-3,4-dihydroquinolin-2(1H)-one (1.38 g) as a colorless crystal. To a solution of 7-methoxy-3,4-dihydroquinolin-2(1H)-one thus obtained (1.38 g) in tetrahydrofuran (30 ml), lithium aluminum hydride (592 mg) was added under ice cooling, heated under reflux for 4.5 hours, and then stirred overnight at room temperature. The reaction mixture was diluted with 28% aqueous ammonia under ice cooling and filtered to remove insoluble materials. The filtrate was evaporated under reduced pressure to remove the solvent. The resulting residue was purified by silica gel column chromatography (eluting solvent: n-hexane:ethyl acetate=20:1 to 9:1) to give the titled compound, i.e., 7-methoxy-1,2,3,4-tetrahydroquinoline (1.18 g) as a yellow oil.

Provenance & Evidence