p-Anisoyl chloride → 4-(p-Methoxybenzoyl)-8-chloro-1,2,3,4,5,6-hexahydrobenzo[f]quinoline

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Reaction Steps

15.0 g (0.06 mol) of 8-chloro-1,2,3,4,5,6-hexahydrobenzo[f]quinoline are dissolved in 150 ml of methylene chloride, treated with 6.68 g (0.066 mol) of triethylamine and 11.2 g (0.066 mol) of p-methoxybenzoyl chloride in 50 ml of methylene chloride are added dropwise thereto at 0°. After stirring at room temperature for 1 hour, the mixture is extracted with water, dried with magnesium sulfate and the solvent is distilled in a vacuum. Crystallization (methylene chloride-ether) gives 4-(p-methoxybenzoyl)-8-chloro-1,2,3,4,5,6-hexahydrobenzo-[f]quinoline as white crystals with melting point 182°-183°.

Provenance & Evidence