反应详情

100 g (0.55 mol) of 6-chloro-3,4-dihydro-2(1H)-naphthalenone are dissolved under argon in 2 l of toluene, treated with 64.0 g of powdered potassium hydroxide, heated to boiling temperature, 165 g of 3-chloropropylamine hydrochloride are added portionwise thereto during 30 minutes and the mixture is boiled on a water separator until educt can no longer be detected in the thin-layer chromatogram. After cooling to room temperature, the mixture is treated with 155 ml of triethylamine. While cooling with ice so that an internal temperature of 25° is not exceeded, the mixture is treated dropwise with 60 ml of acetyl chloride dissolved in 450 ml of toluene. The mixture is stirred at room temperature for 1 hour, extracted with water/methylene chloride and dried with magnesium sulfate. The solvent is distilled in a vacuum and there is obtained 4-acetyl-8-chloro-1,2,3,4,5,6-hexahydrobenzo[f]quinoline in the form of brown crystals which can be used as the crude product for the reaction described hereinafter.

1. temperatureheated
2. additionare added portionwise
3. temperatureWhile cooling with ice so that an internal temperature of 25°
4. extractionextracted with water/methylene chloride
5. dry with materialdried with magnesium sulfate
6. distillationThe solvent is distilled in a vacuum