Pseudomauveine

A dyestuff probably identical -with pseudomauveine has been obtained synthetically by Fischer and Hepp, by action of para-nitrosodiphenylamine on aniline hydrochloride [51]. 

Show how oxidation of aniline by a sequence related to Eq. (1) might lead to the brilliant red-purple dye "pseudomauveine," which has a structure related to Aniline Black. 

Solution The oxidation, shown by equation (1) is initiated by a hydride-ion abstraction. The resulting N-phenylamino cation then adds para to another aniline molecule, which after removal of the proton and complete oxidation, yields, N-phenylquinonediimine. The final structure of pseudomauveine is synthesized via two such oxidation sequences, and then a slight rearrangement to... 

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