13090-99-8Relevant academic research and scientific papers
Synthesis of 9-chloro-1,10-anthraquinone and its reactions with amines
Gorelik,Titova,Gladysheva
, p. 1141 - 1146 (2007/10/03)
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.
Novel, Direct Amination of Anthraquinone by Rhodium(I) Complexes
Mita, Katsuhisa,Yamagishi, Takamichi,Hida, Mitsuhiko
, p. 1036 - 1037 (2007/10/02)
In the presence of certain rhodium(I) complexes, anthraquinone was found to react with amines to give the 1-alkylaminoanthraquinones, along with small amounts of the 1,4-bis(alkylamino)anthraquinones; this direct amination characteristically occurs only at the α-position of anthraquinone.
