1-Aminoanthraquinone → 10-Iminoanthracen-9(10h)-one

Participants

Reaction Conditions

Reaction Steps

A reaction vessel is charged with 5000 parts of nitrobenzene to which are added 428.5 parts of 1,5-dichloroanthraquinone, 670 parts of 1-aminoanthraquinone, 250 parts of anhydrous sodium carbonate and 10 parts of copper(I) chloride. With stirring, the mixture is heated to 190° C. and a further 10 parts of copper(I) chloride are added. After reflux distillation without pressure over 5 hours, the reaction mixture is heated to 240° C. and the pressure rises to 2 bar. Stirring is continued for 4 hours under these conditions. The reaction mixture is cooled and the reaction product is isolated and dried, affording 976 parts (97% yield, based on 1,5-dichloroanthraquinone) of the anthraquinone imide of the formula ##STR2## This anthraquinone imide is converted into a yellow vat dye by a double carbazole cyclisation.

Provenance & Evidence