Dr. Hofmann on the Metamorphoses of Naphthalamine* 227 



analysis of the hydrochlorate and of the platinum salt, which 

 respectively contain 



C42H17N3, HCland 



C42H17N3, HCl, PtClg. 



Among the various metamorphoses which menaphthalamine im- 

 dergoes under the influence of agents, the deportment of this sub- 

 stance with cyanogen has especially engaged the attention of Mr* 

 Perkin. 



Menaphthalamine, like melaniline, absorbs two equivalents of 

 cyanogen, and is converted into a slightly crystalline buif-coloured 

 substance, which retains feebly basic properties. 



The analysis of this body, which, from its composition, may be 

 termed dicymenaphthalamine, has led to the formula 

 C46H,7N3 = C4,H,,N3 + Cy,. 



Dicymenaphthalamine is insoluble in water, moderately soluble in 

 alcohol and ether. It dissolves readily in acids. The latter solution, 

 when precipitated by potassa, immediately after it has been made, 

 yields unchanged dicymenaphthalamine ; but if the solution be 

 allowed to stand for a few moments, a yellow substance is precipi- 

 tated, which is no longer a salt of dicymenaphthalamine. 



The composition of this yellow body, which, in accordance with 

 the terminology adopted in the aniline series, may be called menaph- 

 thoximide, is represented by the following formula — 



and its formation is illustrated by the equation — 



C46 Hi7 N. + 4H0 + 2HC1 = C4, B.,, N3 O4 + 2NH4 CI. 



Dicymenaph- Menaphthox- 



thalamine. imide. 



In fact, the mother-liquor of this substance contains a large amount 

 of ammonia. 



Menaphthoximide may be viewed as binoxalate of menaphthala- 

 mine minus 4 equivalents of water — 



C^^itN^HC^O^, HC^O^- 4H0 = C46Hi,N3 04; 



Binoxalate of menaphthalamine. Menaphthoximide. 



and this view is corroborated by the deportment of the substance 

 with potassa, which reproduces menaphthalamine and oxalic acid. 



From the preceding experiments, it is obvious that the deport- 

 ment of naphthalamine with chloride of cyanogen is perfectly analo- 

 gous to that of aniline. The subsequent metamorphoses of the 

 newly-formed compound also exhibit the same analogy. 



Aniline series. Naphthalamine series. 



Aniline ^12^7 ^ 



Naphthalamine .... C^a ^9 ^ 

 Menaphthalamine . . C42 Hj; Ng 

 Dicymenaphthalamine C^g Hj; Ng 

 Menaphthoximide . . C^q Hjy Ng O4 

 Results of much interest are to be expected from the examination 

 of the products formed by the action of heat on menaphthoximide, 



Q2 



Melaniline .. C26HJ3N3 

 Dicymelaniline Cg^ H^g N^ 

 Melanoximide C30H13N3O4 



