Water → 4-Acetyl-8-chloro-1,2,3,4,5,6-hexahydrobenzo[f]quinoline

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Reaction Steps

229 g (1.04 mol) of 8-chloro-1,2,3,4,5,6-hexahydrobenzo[f]quinoline are dissolved in 2 ml of methylene chloride, treated with 115 g (1.14 mol) of triethylamine and 89.5 g (1.14 mol) of acetyl chloride in 400 ml of methylene chloride are added dropwise thereto at 0°. After stirring at room temperature for 1 hour, the mixture is poured into water, extracted with methylene chloride and the methylene chloride phase is dried with magnesium sulfate. Distillation of the solvent in a vacuum gives a crude product which is suspended in 500 ml of ether and removed by filtration. There is obtained 4-acetyl-8-chloro-1,2,3,4,5,6-hexahydrobenzo[f]quinoline with melting point 106°-108°. Concentration of the mother liquor and chromatography (silica gel/chloroform) gives an additional portion with melting point 106°-108°.

Provenance & Evidence