Synthesis of 9-chloro-1,10-anthraquinone and its reactions with amines

Article abstract of DOI:10.1007/BF02503487

1-Dichlorophosphoryloxy-9,9-dichloroanthrone, a product of the reaction between 1-hydroxyanthraquinone and PCl₅, reacts with primary amines in benzene to give first 1-(diaminophosphoryloxy)-9,9-dichloroanthrones and then the corresponding 9-imines. The reaction in DMF occurs with elimination of the phosphoryloxy group and generation of 9-chloro-1,10-anthraquinone that undergoes amination followed by substitution of the hydrogen atom in position 4 rather than a chlorine atom in position 9, which is the most active position in 2,4,9-trichloro-1,10-anthraquinone. The second step of amination results in 4,9-di(alkylamino)-1,10-anthraquinone. The literature data on obtaining individual 9-chloro-1,10-anthraquinone under the action of bases on 1-dichorophosphoryloxy-9,9-dichloroanthrone were not experimentally supported.