1-アミノ-2-オキシアントラキノンの合成

抄録

1-Amino-2-hydroxyanthraquinone was synthesized from ammonolysis of 1-chloro-2-hydroxyanthraquinone. 1-Chloro-2-aminoanthraquinone in conc. sulfuric acid was diazotized with sodium nitrite and decomposition by heating for 30min. at 150°C yielded 87% of theory of 1-chloro-2-hydroxyanthraquinone, mp 226.9-7.6°C. Ammonolysis of 1-chloro-2-hydroxyanthraquinone was completed by heating for 6 hrs. at 100°C in 15 times of its weight of 28% aqueous ammonia and 0.1 mole copper sulfate catalyst. Alkali insoluble portion and aqueous barium hydroxide solution insoluble portion were removed and recrystallization of the product from 50% aqueous solution of ethanol gave red needles. However, this was not a pure 1-amino-2-hydroxyanthraquinone but contained yellow colored 1-chloro-2-hydroxyanthraquinone and others as impurities from the result of examinations by alumina column chromatography, paper chromatography, and spectrometric analysis. The purity was found to be 93% by spectrometric analysis and this can be utilizable for synthesis of intermediate of anthraquinone-oxazole dyes.