Hydrochloric Acid → 4-[3-Bis(2-hydroxyethyl)aminopropyl]amino-quinoline dinitrate dihydrochloride

Participants

Reaction Conditions

Reaction Steps

A solution of 5.0 g. of 4-[3-bis(2-hydroxyethyl)aminopropyl]amino-quinoline in 5.0 g. of glacial acetic acid is added slowly to a mixture of 15 ml. of acetic anhydride and 5.0 ml. of 90% nitric acid with stirring at minus 5° C. The resulting mixture is allowed to warm to plus 5° C. and after standing for an additional 5 minutes it is treated with an excess of ice-cold aqueous ammonia solution and then extracted with methylene chloride to obtain an amber oil which is dissolved in 5.0 ml. of ethanol and 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 4-[3-bis(2-hydroxyethyl)aminopropyl]amino-quinoline dinitrate dihydrochloride, m.p. 125° C. (decomp.).

Provenance & Evidence