318 Drs. Muspratt and Hofmann on Nitraniline, 



Cl8 { N0 4 } N0 < + 4(K0 ' H0) = Cl2 { N0 4 } N + 4 < K0 ' co ^ + 2TL 



i — * 1 . J: . 



Nitrisatine. Nitraniline. 



On studying however the action of nitric acid upon isatine, 

 we soon found that the yellow powder which is formed is not 

 simply a substitution product of isatine, but belongs evidently 

 to one of the families of bodies containing less carbon, which 

 proceed from the indigo series. It was therefore obvious that 

 by distilling this compound with hydrate of potassa, we could 

 not effect our purpose. 



A third mode for the preparation of nitraniline occurred to 

 us. One of the manifold sources of aniline is the destructive 

 distillation of anthranilic acid, which simply loses 2 equiva- 

 lents of carbonic acid ; isomeric with this acid is salicylamide, 

 recently described by Cahours*. The composition of these 

 two bodies is represented by the formula Ci 4 H 7 N0 4 . Now 

 if the salicylamide underwent the same decomposition by 

 heat as anthranilic acid, it might obviously be supposed that 

 the nitraniline would result from the distillation of nitrosali- 

 cylamide, a substance also lately prepared by Cahours. 

 C I4 H s O. NH 9 — 2C0 9 = C„ H„ NH, or C„ H, N 



Salicylamide. Aniline. 



C »{ N0 4 } °" NH « ~ 2C °3 = C »{ N0 4 } NH * or C » { NO, } N " 



v , 1 ( ir ____j 



Nitrosalicylamide. Nitraniline. 



There were some researches made in this direction, the results 

 of which we published at the beginning of last yearf. 



The exceedingly small amount of aniline, however, which 

 the distillation of salicylamide had yielded (the principal pro- 

 ducts being hydrate of phenyle and ammonia), could never 

 warrant a similar treatment of nitrosalicylamide, in order to 

 obtain a sufficient quantity of nitraniline for analysis and a 

 complete study of its properties. 



There yet remained to us one resource. We have already 

 mentioned a compound which is produced by the continued 

 action of nitric acid upon nitrobenzole, i. e. dinitrobenzole, 



JH 4 



J \2IV 



Cl2 i 2N0 4 



which we may consider as nitrobenzole, in which a second 

 equivalent of hydrogen is replaced by hyponitric acid. Che- 

 mists are well-acquainted with the interesting transformation 

 which nitrobenzole suffers with reducing agents. By assuming 



* Ann, der Chem. und Pharm. vol. xl. p. 64. 

 t Phil. Mag., vol. xxvi. p. 581. 



