Sodium Iodide → 1-[2-(1,3-Dioxolan-2-yl)ethyl]-7-methoxy-4-methylquinolin-2(1H)one

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Reaction Steps

In N,N-dimethylformamide (15 ml) was dissolved 7-methoxy-4-methylquinolin-2(1H)one (1.5 g, 6.06 mmol), sodium iodide (2.3 g, 15.9 mmol) was added thereto under cooling on ice and lithium hydride (188 mg, 15.9 mmol) was gradually added thereto. After stirring for 1 hour under cooling on ice, 2-(2-bromoethyl)-1,3-dioxolane (1.6 ml, 15.9 mmol) was gradually added thereto. The reaction solution was stirred overnight at room temperature and then the extract was partitioned into ethyl acetate-water, whereby the organic layer was separated. The obtained organic layer was washed with water and saturated sodium chloride solution and dried over anhydrous sodium sulfate. The solvent was removed under reduced pressure and the obtained residue was purified by silica gel column chromatography (hexane/ethyl acetate) to yield 1 g (57%) of the title compound.

Provenance & Evidence