79693-24-6Relevant academic research and scientific papers
Etudes sur les meso-aminoanthracenes. VIII. L'amino-10 anthracenecarboxylate-9 de methyle. Oxydation et diazotation
Rigaudy, Jean,Ahond, Monique,Barcelo, Jacques,Valt-Taphanel, Marie-Helene
, p. 223 - 230 (2007/10/02)
Methyl 10-amino-9-anthracenecarboxylate, the preparation of which is described, hardly autoxydizes, and the corresponding 10-imino-9-hydroperoxyde is obtained more easily by photosensitized oxygenation.On the other hand, it is fairly sensitive to electron-abstracting oxydants like PbO2, giving its unsymmetrical dehydrodimer.It cannot be diazotized by the usual nitrosating agents, such as isoamyl nitrite, which lead mostly to 10-methoxycarbonyl-10-nitro-9-anthron.With nitric oxyde in ether, diazotization is also limited owing to an extensive competing reduction to methyl 9-anthroate.Yet, it is shown that a treatment of the amine in ethereal solution by N2O4 gives the corresponding diazonium salts in reasonable yields, the production of nitro-anthron being restricted in these conditions.
