Reactions of 1, 5-dichloroanthraquinone (1) with various nucleophiles were examined to evaluate possibilities for selective substitution. 1-Amino-5-chloroanthraquinone was obtained from 1 by reaction with (a) sodium azide in dimethyl sulfoxide and (b) ammonia in the presence of potassium fluoride, but 1 with potassamide in ammonia gave 3- chlorobenzoic acid. Conditions were found for preferential substitution in reactions of 1 ...