Hydrochloric Acid → 9,10-Anthracenedione, 1,4-bis((2-(diethylamino)ethyl)amino)-

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Reaction Conditions

Reaction Steps

A mixture of 5 g (0.021 mol) of 1,4-dihydroxyanthracene-9,10-dione and 2 g (0.014 mol) of sodium dithionite in 20 ml water is stirred whilst heating under nitrogen at 90° C. until the mixture turns from orange to brown indicating the presence of 2,3-dihydro(leuco)-1,4-dihydroxyanthracene-9,10-dione. To this reaction mixture is added dropwise 20 g (0.17 mol) of 2-(diethylamino)-ethylamine over a 30 minute period. The mixture is heated at 50°-55° C. for 2 hours and 20 ml of ethanol are added. The solution is then aerated and 200 ml of 2M hydrochloric acid are added. The acidic mixture is washed with 3×200 ml of diethylether followed by 3×200 ml of chloroform. The aqueous phase is made alkaline by the addition of sodium hydroxide solution and extracted with 3×200 ml chloroform. The mixture is evaporated in vacuo to a 5 ml volume and subjected to flash chromatography using a column of 70-230 mesh (60 A) silica gel (SiO2) and an eluting solvent of chloroform followed by chloroform:methanol (1:1 v/v). The blue black material removed from the column in chloroform/methanol is evaporated in vacuo to yield 0.7 g of the title compound, m.p. 107.5°-108.5° C.; λmax λmax (deionised water) (E/cm/M) 256 nm (50950), 584 nm (18650).

Provenance & Evidence