groups a hydroxy group a cyano group an acylamino group having from 1 to 6 carbon atoms in the acyl moiety thereof e g as hereinbefore described an alkylsulfonamido group preferably having from 1 to 6 carbon atoms in the alkyl moiety thereof e g as hereinbefore described a halogen atom preferably chlorine and bromine atoms a nitro group and so on the selection of the appropriate substituent substituent position and number of substituted groups should be made by considering the color tone the solubility the light stability and the transfer efficiency of the dye developers which will be obtained when the compounds prepared in the present invention are reduced preferred diazonium compounds which can be employed in the practice of the present invention include benzene diazonium compounds naphthalene diazonium compounds and heterocyclic diazonium compounds represented by the following formulae wherein although the anion in these examples is shown to be a chlorine ion or acetate ion the anion is not restricted to the above two specific ions because the anion can be altered by the specific acids used str20 the diazo coupling reaction of quinone residue containing couplers with diazonium compounds was not known until now it is surprising that the desired quinone residue containing azo dye could be prepared when a diazo coupling reaction was attempted under well known conditions suitable for a conventional diazotization as described in for example chemistry of new dyes and synthetic dyes supra and ryohei oda lecture on experimental chemistry vol 20 maruzen co ltd tokyo 1957 namely the following various conditions will be optionally required when they are allowed to react with each other 1 the quantity of the diazonium compound added to the quinone residue containing coupler should range from about 0 1 to.