8-Chloro-2-phenyl-1,3,4,5-tetrahydrobenz[cd]indol-5-one → 2-Phenyl-1,3,4,5-tetrahydrobenz[cd]indol-5-one

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Reaction Steps

A portion (2.4 g) of the compound obtained in Example 60 was dissolved in a solution of potassium hydroxide (3 g) in methanol (150 ml) and to the solution was added 10% palladium-carbon (500 mg). The mixture was stirred for 30 minutes at room temperature under a hydrogen atmosphere. The catalyst was filtered off and the filtrate was concentrated under reduced pressure. The residue was dissolved in ethyl acetate, washed with water and saturated aqueous solution of sodium chloride and dried over anhydrous sodium sulfate. The solvent was distilled off under reduced pressure and the residue was purified by silica gel column chromatography (ethyl acetate/hexane=10:1-2:1) to yield 700 mg (39%) of the titled compound.

Provenance & Evidence