1863.] 



Dr. Hofmann o?z Kinone. 



5 



residue which is left on evaporating this Hquid with hydrochloric acid, 

 is a mixture of hydrochlorate of aniline and hydroMnone, They are easily 

 separated hy treatment with ether, which dissolves the hydrokinone, 

 leaving the aniline-salt as an insoluble residue. The ethereal solution, 

 when evaporated, yields colourless needles of hydrokinone possessing all 

 the characteristic properties which distinguish this remarkable body. 

 Addition of ferric chloride to their aqueous solution produces at once the 

 green prisms, with golden lustre of the intermediate hydrokinone. 



The action of kinone upon aniline is therefore represented by the follow- 

 ing equation : — 



2 C, H, N + 3 C3 H, 0,= C,3 H,, 0, + 2 C, O,. 



V 



Aniline. Kinone. Brown crystals. Hydrokinone. 



The study of this reaction has induced me to repeat an experiment men- 

 tioned by M. Hesse in his beautiful researches on the kinone group*. 



By submitting aniline to the action of chloranile (tetrachlorkinone), 

 M. Ilesse has obtained a compound crystallizing in reddish-brown scales, 

 the general properties of which resemble those of the kinone derivative 

 above described. The composition of the compound formed with chlor- 

 anile M. Hesse represents by the formula 



C,,H3,C1,0,N,= (C. Cl,OJ'aN,. 



H, J _ 



I cannot confirm this somewhat complicated expression. In studying the 

 action of chloranile upon aniline, I have observed all the phenomena de- 

 scribed by M. Hesse : the compound formed had all the properties which 

 he assigns to it, but was found on analysis to contain about 2 per cent, of 

 carbon less than he had observed. The substance examined by me con- 

 tained 



c,, H,,ci,N,o,=(c„ CI, o J" In,. 



H, J 



This is the formula of the kinone derivative with two atoms of hydrogen 

 replaced by chlorine. The action of chloranile on aniline is therefore, in 

 a measure, analogous to that of kinone. 



4 C3 H, N + C, CI, 0,= H,, CI N, + 2 C, H, N, HCl 



V 



Aniline. Chloranile. Hydrochlorate 



of aniline. 



The formula which I propose to substitute for that of M. Hesse is 

 moreover supported by the result obtained in studying the deportment of 

 chloranile under the influence of ammonia. This gives rise to the formation 

 of chloranilamide discovered by Laurentf, and represented by the formula 



(c„aoj"] 



CJ-I,C!,KO,= H, In,. 



H, J 



* Ann. Chem. Pharm. cxiv. p. 307. t Laurent, xix. 323. 



