Ammonia → 2-[3-Bis(2-hydroxyethyl)aminopropyl]amino-quinoline dinitrate dihydrochloride

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Reaction Steps

A solution of 5.0 g. of 2-[3-bis(2-hydroxyethyl)aminopropyl]amino-quinoline in 5.0 g. of glacial acetic acid is added slowly to a stirred cooled (-5° C.) mixture of 15.0 ml. of acetic anhydride and 5.0 ml. of 90% nitric acid. Stirring is continued for 20 minutes after addition and 500 ml. of diethyl ether added to obtain an oil which is added to an excess of cooled (0° C.) aqueous ammonia solution. The resulting mixture is extracted with ethyl acetate, the organic phase dried and concentrated in vacuo to obtain an oil which is treated with a slight excess of hydrogen chloride in ethanol. Addition of diethyl ether yields a solid which is recrystallized from methanol/diethyl ether to obtain 2-[3-bis(2-hydroxyethyl)aminopropyl]amino-quinoline dinitrate dihydrochloride, m.p. 112° C. (decomp.)

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