1?0 Proceedings of the Royal Irish Academy. 



remain in stoppered flasks at the room temperature for several weeks, in 

 eacli case the contents of the flask were poured into water, and the solid 

 which separated was filtered, washed, and dried. It proved in each instance 

 to be unchanged phenyl-aceto-2-naphthalide. 



C. Ac/ion of If Uric Acid on Phenyl-18-Naphthylamme. 



1. Concentrated Nitric Acid. 



On addition of colourless, concentrated nitric acid (sp.gr. 1.43) to phenyl- 

 2-naphthylaniine, a violent reaction set in with separation of a dark-coloured 

 resinous mass. The mixture was poured into water, filtered, and the separated 

 solid was washed well with water. When dried, it was extracted with 

 benzene in a Soxhlet apparatus. The benzene was distilled, and the solid 

 residue was recrystallised from glacial acetic acid. After a number of 

 rstallisatione from acetic acid, red prisms were obtained which softened 

 at 17s ('. and decomposed at about 210 C. In this method, even when the 

 nitration was conducted in an ice bath, much resin was found. When the 

 nitration was conducted in ethereal solution, a much better yield of the 

 compound was obtained. 



Nitric acid (4 mols) was added bo an ethereal solution of phenyl-2- 

 uaphthylamine so .slowly that the temperature did not rise appreciably. The 

 ether was allowed bo evaporate at a low temperature, and the residue was 



stallised from glacial acetic acid. The substance, which separated almost 

 quantitatively, & of red prismatic crystals, melting about 210 C. with 

 decomposition, and gav< analysis the following results: — 



0*1522 grams of tie- Mibstance gave 20 c.c. of moist nitrogen 

 at 16 ( '. and 750 m. m. p. 



responding to N 15 - 3. 

 I .11 \,ii requires N 1 5*8. 



The substance was therefore a trinitro-phenyl-2-naphthylamine. 



2. Fn I 



A ut 5 grams of phenyl- 2-naphthylamine were dissolved in 40-50 grams 



of glacial acetic acid am ms of nitric su id (sp. ji. l"43) were added 



' tn Branding overnight brown crystals separated, The crystals were filtered. 

 and washed with cold water. The solid was next boiled with 10 c.c. of 

 glacial a id foi ben minutes, and the acetic acid solution was separated 



from the yellow undissolved solid by filtration. The red substance which 

 irated from the acetic acid on cooling was probably identical with the 

 dinitro compound obtained by StreifJ 



