Ryan and Dkumm — Derivatives of Phenyl-2-Naphthylaminc. 169 



solution for two hours. The mixture was allowed to remain in a stoppered 

 flask for eight to ten days. At the end of this time, about three grams of a 

 white, crusty solid had separated from the alcoholic solution, the latter 

 having in the interval acquired a red tint. The solid was filtered and 

 recrystallised from glacial acetic acid. It consisted of yellow prisms, which 

 melted at 242-243° C, and gave on analysis the following results : — 



0-1470 grams of the substance gave 20'2 c.c. of moist nitrogen at 

 15-5° C. and 757 m.m.p. 



corresponding to N 16'0 

 C, 6 H,„N,,0 6 requires N 15-8 



The compound was therefore a trinitro derivative of phenyl -2-naphthy- 

 lamine, and was subsequently found to be identical with 2'.4'.l-trinitro- 

 pheiiyl-2-naphthylamine. 



The parent liquid from which the latter substance had crystallised was 

 found to contain another trinitro derivative of phenyl-2-naphthylamine. It 

 was precipitated from the solution by addition of water, and recrystallised 

 from a little acetic acid. It consisted of orange prisms, which melted at 

 179-180° C, and gave on analysis the following results: — 



04428 grams of the substance gave 198 c.c. of moist nitrogen at 

 18° C. and 748 m.m.p. 



corresponding to N 15 - 76 

 C 16 H l0 N 4 O 6 requires N 15 '8 



B. Action of Nitric Acid on Phenyl- Aceto-2-Naphtlioliil * . 



1. Cold Concentrated Nitric Acid. 



When pure crystallised phenyl-aceto-2-naphthalide was triturated with 

 about three parts of nitric acid (sp. gr T43), it gradually dissolved in the 

 acid, forming a red syrup. On pouring the syrup into ten volumes of water a 

 yellow mass was precipitated. The semi-solid substance was filtered, washed 

 well with water, dried, and recrystallised from xylene, from which it separated 

 in the form of slightly yellow cubical crystals melting at 119-120° C. The 

 yield of the compound was almost quantitative. The substance proved to be 

 identical with the compound of the same melting-point formed by the action of 

 nitrogen peroxide on the stabiliser in moist ether solution. 



2. In Acetic Acid Solution. 



Quantities of nitric acid corresponding to 1-6 molecular amounts of the 



acid to one molecular amouut of the stabiliser were added to a live per cent. 

 solution of the latter in glacial acetic acid. The solutions were allowed in 



