Sodium hydride → 5,6-dihydro-6-(2-methoxycarbonylphenyl)methoxy-2-(2-phenylethyl)-4H-imidazo[4,5,1-ij]quinoline

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Reaction Steps

A portion (1.15 g) of 60% sodium hydride was added to 50 mL of anhydrous N,N-dimethylformamide (DMF) in an argon atmosphere; 2.0 g of 5,6-dihydro-2-(2-phenylethyl)-4H-imidazo[4,5,1-ij]quinolin-6-ol obtained in Example 4 was dissolved in anhydrous DMF (40 mL) and the solution was added dropwise to the first mentioned solution at room temperature. After stirring for 1 hr at room temperature, a solution of methyl o-bromomethylbenzoate (6.6 g) in anhydrous DMF (40 mL) was added dropwise and the mixture was stirred for 1 hr. The reaction solution was poured into ice water (500 mL), and extracted with ethyl acetate, 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 a yellow oil (2.38 g).

Provenance & Evidence