Water → N-[6-Chlorohexyl]-6-methoxy-4-methyl-8-quinolinamine

참여 물질

반응 단계

To a stirred solution of 7.8 g (0.027 mole) of 6-[(6-methoxy-4-methyl-8-quinolinyl)amino-1-hexanol in 90 ml of dichloromethane at 5° was added dropwise a solution of 1.9 ml (0.03 mole) of thionylchloride in 25 ml of dichloromethane. The mixture was allowed to warm to room temperature overnight, poured into iced water, and made basic with concentrated ammonium hydroxide. The resulting emulsion was filtered and the layers then separated. The organic portion was washed, dried, and concentrated to afford 7.9 g (96%) of crude product which was used in the next step without further purification. TLC(silica--thyl acetate) indicated that the product, Rf=0.65, was slightly contaminated with the starting hexanol, Rf=0.4.

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