ClC1C=CC=CC=1[N+:8](=[N:10][C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=1[Cl:17])[O-:9].[OH-:18].[Na+].O.NN>CO.[Ni].O>[Cl:17][C:12]1[CH:13]=[C:14]([C:14]2[CH:15]=[CH:16][C:11]([NH2:10])=[C:12]([Cl:17])[CH:13]=2)[CH:15]=[CH:16][C:11]=1[NH2:10].[N:8]([OH:9])=[O:18]53.4 g of 2,2'-dichloroazoxybenzene are stirred in 60 ml of methanol. 0.6 g of sodium hydroxide and 11.8 ml of hydrazine hydrate are added and the mixture is warmed to 65° C. After Raney nickel has been added (a total of about 0.05 g in 2-3 portions) vigorous evolution of nitrogen starts. The reduction has ended after 30 minutes. The mixture is cooled to 10° C. and diluted with water and the 2,2'-dichlorohydrazobenzene which has crystallised out is filtered off and washed with water until neutral. After the rearrangement to 3,3'-dichlorobenzidine and tetrazotisation with nitrous acid, a yield of 86% of theory is obtained.
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