Methyl iodide → 5,6-dihydro-6-methylthio-2-(2-phenylethyl)-4H-imidazo[4,5,1-ij]quinoline

Participants

Reaction Steps

The mixture of 60% sodium hydride (245 mg) and anhydrous tetrahydrofuran (20 mL) under an argon atmosphere was added dropwise the solusion of 5,6-dihydro-2-(2-phenylethyl)-4H-imidazo[4,5,1-ij]quinoline-6-thiol (0.45 g) obtained in Example 28 in anhydrous tetrahydrofuran (20 mL) at room temperature. After stirring for 1 hr at room temperature, methyl iodide (0.95 mL) was added dropwise and the mixture was stirred for 30 min. Ice water was added to the reaction solution and stirred; thereafter, the mixture was extracted with ethyl acetate and the organic layer was washed with saturated brine and dried over anhydrous sodium sulfate. The solvent was removed under reduced pressure and the residue was purified by silica gel column chromatography (eluent: hexane/ethyl acetate) to yield the titled compound as colorless crystals (356 mg).

Provenance & Evidence