276 THE AROMATIC PRIMARY AMINO GROUPiwhen l,6-dinitronaphthylamine-2 is diazotized in concentrated sulfuricacid and then diluted with ice-cold water, the diazo oxide is precipitated.N2+HSO4-The reaction occurs so rapidly that attempts to deaminate by the usualprocedures give little or no 1,6-dmitronaphthalene.63'MIn consequence of hydrolytic cleavage, a diazo oxide also is obtainedfrom the isomeric l,8-dinitronaphthylamine-2. Here, however, elimina-tion of the nitro group is a comparatively slow reaction so that treat-ment with ethanol gives, a satisfactory yield of 1,8-dinitronaphtha-,lene.63-64*A dearth of quantitative information about the rate of diazo oxide for-mation makes it impossible to generalize about the importance which isto be attached to this side reaction. However, it appears that in manyinstances the reaction is a comparatively slow one, so that anhydrousconditions are unnecessary. In this connection it is significant that
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