332 , Proceedings of the Royal Irish' Academy . : 



2. Action of Nitrosophenylurethane on Toluylenediamine Hydrochloride. 



A warm solution of 2 g. of nitrosophenylurethaue in 30 c.c. of methylated 

 spirit was added gradually to a similar solution of l'o7 g. of 9ft-toluylene- 

 diamine, to which an amount of hydrochloric acid had been added, sufficient 

 to form the monohydrochloride of the amine. The bright-red coloured 

 solution thus got was boiled for five minutes ; but as no separation of solid 

 occurred on then cooling the solution, the latter was concentrated carefully 

 to about half its original volume. On cooling the solution, and allowing it 

 to remain for some time at the room temperature, dark-blue prismatic 

 crystals separated. A black, tarry mass was obtained from the filtrate from 

 these crystals. 



The dark-blue crystals did not melt below 340° C. They dissolved in 

 water, forming a deep-purple solution, and when this solution was diluted, 

 the colour changed to apricot. The substance gave on analysis the following 

 results : — 



0H05 g. substance gave 20'7 c.c. moist N" at 15-5° C. and 767 m.m., 

 corresponding to N 22-1 ; 



0-2519 g. substance gave 0-1253 g. AgCl, 



corresponding to CI 12-3. 

 C^HhN^HCI requires N 21-4, CI 13-5. 

 CieH.eNAHC] requires N 16-7, CI 10-6. 



The percentages of nitrogen and chlorine are much too high for an 

 indamine derived from the original urethane. The analysis indicates, on the 

 other hand, that the body is the monohydrochloride of an indamine derived 

 from nitrosoaniline and toluylenediamine contaminated with a small amount 

 of the free base. 



When dilute potash was added to an aqueous solution of the indamine 

 hydrochloride the indamine was precipitated as a reddish-brown amorphous 

 solid. The free base, which had a marked fluorescence, was purified by 

 solution in alcohol. Acids readily redissolved it, forming deeply-coloured 

 solutions. It gave on analysis the following results : — 



0-1384 g. substance gave 28-6 c.c. moist N at 16-5^ C. and 762 m.m., 

 corresponding to N 24-1. " 



Ci^HuNj requires N 24-7. 

 CisHj,N40., requires N 18-8. 



A crystalline, straw-coloured, neutral substance was sometimes obtained 

 in the experiments with nitrosophenylurethaue and wi-toluylenediamine. 



