74 Royal Society : — 



have hitherto been produced only by the action of potash upon 

 bromisatine and chorisatine, the indirect method, by which they were 

 originally obtained by Dr. Hofmaon ; it appeared therefore of some 

 interest to ascertain whether the bodies generated directly from 

 compounds of phenylamine would exhibit differences in their proper- 

 ties similar to those which distinguish alpha- and beta-nitrophenyl- 

 amine. 



With the view of deciding this question experimentally, I have 

 submitted acetylphenylamide to the action of bromine and chlorine, 

 in the hope of thus forming directly from phenylamine the bromi- 

 nated and chlorinated compounds in question. 



Action of Bromine on Acetylphenylamide. 

 A cold aqueous solution of acetylphenylamide, when agitated with 

 bromine gradually added in small quantities until the yellow colour 

 imparted to the liquid no longer disappears, furnishes a crystalline 

 compound difficultly soluble in cold, but easily recrystallizable from 

 boiling water. The substance consists chiefly of monobrominated 

 acetylphenylamide 



(C 6 H 4 Br) ) 

 (C,H 8 BrNO = (C,H 3 0) [ N, 

 "H J 



which is however invariably mixed with small quantities of dibro- 

 minated acetylphenylamide 



(C e II 3 Br.,) 1 

 (C,H 7 Br 2 NO = (aH 3 0)" I N. 

 "H J 



T have not been able to find a method of separating these two 

 bodies perfectly. 



The brominated compound is readily attacked by potash. On 

 distilling the mixture, the vapour of water carries over a volatile 



phenylamide may be used for this purpose with considerable advantage. A solution 

 of the compound in cold fuming nitric acid yields, on the addition of water, a 

 crystalline difficultly soluble precipitate, which is easily obtained pure byrecrystal- 

 lization. This substance contains 



[C 6 (II 4 N0 2 )]1 



II s N 2 4 =(C 2 H 3 2 ) I 



H J 



and yields, when heated with potassa, the beta-nitrophenylamine of Arppe with 

 all its properties. I may here recall a former observation, which has now become 

 perfectly intelligible. When studying the action of nitric acid upon melaniline, 

 I found (Chem. Soc. Mem. t. i. 305) that the dinitromelaniline, which is thus 

 formed, essentially differs from the dinitromelaniline obtained by submitting 

 nitrophenylamine (alpha-) to the action of chloride of cyanogen. The two nitro- 

 bases, which are both expressed by the formula 



stand to each other in the same relation which obtains between alpha-nitro- 

 phenylamine and beta-nitrophenylamine. In fact, 1 have since found that the 

 distillation of the nitro-base, obtained by treating alpha-nitrophenylamine with 

 chloride of cyanogen, furnishes alpha-nitrophenylamine ; whilst beta-nitrophenyl- 

 amine may be detected amongst the products of the distillation of the dinitromel- 

 aniline which is formed directly from melaniline by means of nitric acid. — A. W. II. 



