402 Dr. Hofmann on the MetamorpJioses of Indigo. 



Chloraniline thus gives, under the same circumstances, as 

 was to be expected, the same products of decomposition as 

 anihne. 



Action of Chlorine o?i Chloraniline, 



At the commencement of this memoir are given the facts 

 observed by the action of chlorine on aniline. The chlori- 

 nated base suffers precisely the same decompositions. There 

 are formed chlorophenissic acid and a neutral body, the latter 



being trichloraniline, Ci2< r^^ ?-N. I shall return immedi- 

 ately to its preparation and its properties. 



Action of Bromine on Chloraniline. 



By mixing aniline with bromine, heat and hydrobromic 

 acid are disengaged, and there is formed Fritzsche's bromani- 



loid (tribromaniline), C12-I T>t r^. The chlorinated base 



suffers the same decomposition with bromine. The product 

 differs from the foregoing only in containing chlorine. It has 

 the following composition, as we shall see afterwards : — 



Action of Nitric Acid on Chloraniline. 



The decomposition produced in the chlorinated base by 

 nitric acid I have unfortunately as yet but incompletely 

 studied, although this point would have been of particular 

 interest to have cleared up satisfactorily. 



By the action of nitric acid aniline is transformed into car- 

 bazotic acid. It is in the highest degree probable that by the 

 action of this oxidizing agent on chloraniline picric acid is 

 formed, in which 1 equiv. of hydrogen is replaced by 1 of 



chlorine, having the formula Cjg^ CI j^ O + HO. By add- 



L3NO4J 



ing concentrated nitric acid to the chlorinated base, a lively 

 reaction takes place, the fluid remains for some time boiling 

 without the application of external heat, evolves nitrous acid, 

 and becomes dark red, and finally black and opake. By con- 

 tinued action it becomes again transparent, and by allowing 

 the scarlet red fluid to cool there sometimes separate golden 

 yellow needles, which are very similar to the nitropicric acid. 

 No trace of chlorine can be then detected in the fluid by ni- 

 trate of silver. 



