ChemInform Abstract: Synthesis of 9-Chloro-1,10-anthraquinone and Its Reactions with Amines.

✍ Scribed by M. V. GORELIK; S. P. TITOVA; T. H. GLADISHEVA

• Publisher: John Wiley and Sons
• Year: 2010
• Weight: 40 KB
• Volume: 29
• Category: Article
• ISSN: 0931-7597
• DOI: 10.1002/chin.199837108

✦ Synopsis

Synthesis of 9-Chloro-1,10-anthraquinone and Its Reactions with Amines.

-Reaction of 1-hydroxy-9,10-anthraquinone (I) with PCl 5 affords 1-dichlorophosphoryloxy-9,9-dichloroanthrone (II) which on reaction with cyclohexylamine in benzene undergoes amination of the phosphoryloxy group to give compound (IV). This compound (IV) is further aminated in refluxing toluene affording 9-imino-1-diaminophosphoryloxyanthrone (VI). The reaction with aniline does not stop at the first amination step and provides the corresponding 9-imino analogue (IX) immediately. The amination of 9,9-dichloro-1-dichlorophosphoryloxyanthrone (II) in DMF starts at the free position 4 to afford 4-amino-9-chloro-1,10-anthraquinone (XI), while the second amination step proceeding at position 9 is realized in refluxing benzene. The amination of compound (II) in DMF is proposed to go via 9-chloro-1,10anthraquinone, which can not be isolated in pure form. -(GORELIK, M. V.;