1,5-Dichloroanthraquinone → 9,10-Anthracenedione, 1,5-bis((2-(diethylamino)ethyl)amino)-

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Reaction Steps

A solution of 5.52 g (0.02 mol) of 1,5-dichloroanthracene-9,10-dione in 23.2 g (0.2 mol) of 2-(diethylamino)ethylamine is heated at reflux temperature for 4 hours. The mixture is cooled in an ice-bath and 100 ml concentrated hydrochloric acid is added with stirring. This acidic mixture is extracted with three aliquots of 200 ml of diethylether followed by three aliquots of 200 ml of chloroform. The aqueous layer is collected and made alkaline with sodium hydroxide solution, extracted into chloroform and evaporated in vacuo at 30° C. The oily residue is washed with water, dissolved in methanol and titrated with hydrogen chloride in dry diethyl ether to give a precipitate which is dried to yield 5.2 g of the title compound as the hydrochloride in the form of a dark red solid, m.p. 158.5°-159.5° C.; λmax (deionised water) (E/cm/M) 231 nm (34280), 516 nm (10690).

Provenance & Evidence