Organic Lab Reactions 281

Organic Lab Reactions 281 - 276 THE AROMATIC PRIMARY AMINO...

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276 THE AROMATIC PRIMARY AMINO GROUP i when l,6-dinitronaphthylamine-2 is diazotized in concentrated sulfuric acid 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 usual procedures give little or no 1,6-dmitronaphthalene. 63 ' M In consequence of hydrolytic cleavage, a diazo oxide also is obtained from 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 is to be attached to this side reaction. However, it appears that in many instances the reaction is a comparatively slow one, so that anhydrous conditions are unnecessary. In this connection it is significant that diazotized picramide, which is reported to be very unstable in the
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