(3-Bromopropyl)benzene → 6-(2-Chlorophenyl)-3-methyl-2-(3-phenylpropyl)-4,5,6,7-tetrahydroindazol-4-one

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Reaction Steps

To a suspension of 60% sodium hydride (0.068 g, washed with hexane thrice) in dimethylformamide (10 ml) was added a solution of 6-(2-chlorophenyl)-3-methyl-4,5,6,7-tetrahydroindazol-4-one (0.4 g) in dimethylformamide (2 ml) at 0° C., and the mixture was stirred at room temperature for 40 minutes. To the mixture was added 3-phenylpropyl bromide (0.32 g), and the mixture was stirred at the same temperature for 19 hours. Under reduced pressure, the solvent was evaporated, and the residue was dissolved in ethyl acetate. The solution was washed with water and saturated brine, dried with magnesium sulfate and concentrated under reduced pressure, and the residue was purified with silica gel column chromatography (ethyl acetate-hexane) to give 6-(2-chlorophenyl)-3-methyl-1-(3-phenylpropyl)-4,5,6,7-tetrahydroindazol-4-one (0.20 g) as colorless crystals and 6-(2-chlorophenyl)-3-methyl-2-(3-phenylpropyl)-4,5,6,7-tetrahydroindazol-4-one (0.26 g) as oil.

Provenance & Evidence