168 Proceedings of the Royal Irish Academy. 



Ortho-nitro-bromo-benzene, however, could not be made to interact with 

 2-naphthylamine, nor ortho-nitraniline with 2-ehloro-naphthalene, even under 

 the conditions of the Goldberg reaction. 



EXI'EKIMENTAL. 



A. Action <;/ Nitrogen Peroxide on Phenyl- Aceto-2-Naphthalide. 



1. In Anhydrous Ether Solution. 



Nitrogen peroxide, prepared by heating dry had nitrate, was passed for 

 about an hour through a solution of dry, recrystallised phenyl-aceto-2-naph- 

 thalide in anhydrous ether. The mixture was kept in a stoppered flask for a 

 few days, and the ether was then evaporated at a low temperature. The 

 phenyl-acetO-2-uaphthalide was recovered unchanged. 



2. In Moist Etht /• Solui 



A current of nitrogen peroxide was passed through a solution of phenyl- 

 bo-2-naphthalide in moist ether for half an hour. On evaporation of a 

 portion of the ethereal solution and on recnstaliisation of the residue from 

 benzene, phenyl-2-naphthylamine was obtained in the form of white prisms 

 melting at L07 ' , One action, therefore, of the mixed oxyacids of nitrogen, 

 formed from the nitrogen peroxide and the water present in the moist ether, 

 consisted of the conversion of part at least of the aceto-naphthalide into 

 the free amine 



The main portion of the ethereal solution was allowed to remain over- 

 night, and v. allowed t<> evaporate at the room temperature. The 

 deep yellow, oily mass which rem tei several recrystallisations from 

 boiling xylene, afforded colourless, cubical melting at 119-120°C, 

 which gave on analysis the following results: — 



1 940 - _ ive 17 cc of moist nitrogen at 16" C. 



and 771 m.m.p 



corresponding to X 10*7 

 C,,H ,N.< >; req ires N 10*6 

 I 11 .X. 1 I requin - N 9*15 



The compound analysed was therefore a mononitro derivative of phenyl- 

 2-uaphthylamiiie. 



■i. I .! 



A - _ imsofphi -2-naphthalide were dissolved in 200 cc ol 



absolute alcohol, and a current of nitrogen peroxide was led through the 



