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

Participants

Reaction Steps

A solution of 3,4-dihydrocarbostyril (20 g) in DMSO (100 ml) is added to a suspension of KOH (31.4 g) in DMSO (50 ml). Methyl iodide (39.7 g) in DMSO (25 ml) is added to the reaction mixture and the mixture is stirred under an atmosphere of N2 at RT. After 2 hours a second portion of methyl iodide (20 g) is added and after 3 hours a third portion of methyl iodide (20 g) is added and stirring continued for 4.5 hours. The reaction mixture is diluted with chloroform (200 ml), quenched with sat'd aq. NH4Cl, separated, extracted with chloroform, washed with H2O and dried. The organic extracts are filtered and concentrated in vacuo affording the desired product as an oil.

Provenance & Evidence