Ryan and Drdmm — Derivatives of Phenyl-8-Naphthylamine. 173 



3. Nitro-'2-Xii jilillijiln mi in . 



The ace to -naphthalide corresponding to l-nitro-2-naphthylamine had heen 

 previously obtained by Kleemau (Ber. d. Dtsoh. Chern. Ges. XIX, 1S86, 

 p. 338), and was obtained by us by nitration of aceto-2-naphthalide (20 grains) 

 by means of concentrated nitric acid (10 grams) in the presence of acetic acid 

 ('24 grams). The mixture was allowed to remain at the room temperature 

 for twelve hours. The yellow, prismatic solid, which separated, when 

 recrystallised from absolute alcohol, melted, as Kleeman (loc, tit.) stated, at 

 123-1 24° C. 



The amine was prepared from the naphthalide by hydrolysing the latter 

 with alcoholic hydrochloric acid. 



Fifteen grams of the naphthalide were dissolved in 200 c.c. of alcohol, and 

 the solution was heated with 30-40 c.c. of concentrated hydrochloric acid for 

 about three hours under a reflux condenser. On evaporating the mixture, 

 orange-red prisms separated which, after recrystallisation from alcohol, 

 consisted of dark-brown prisms melting at 123-124° C. 



4. 2'. 4'. 1-Trinitro-Phmyl- 2-Naphthylamine. 



Unlike naphthylamine itself, l-nitro-2-naphthylamine did not couple with 

 2.4-dinitro-l-chloro-benzene when heated in alcoholic solution. Accordingly, 

 the Goldberg method was tried, and with good results. 



Four grams of 2.4-dinitro-l-chloro-benzene were heated with 4 grams of 

 l-nitro-2-naphthylamine in 1 c.c. of nitrobenzene in the presence of 1/5 grams 

 of dry potassium carbonate, and traces of copper-dust and potassium iodide. 

 The mixture was kept at a temperature of 190-200° C. for eight hours. The 

 crude compound, which remained after the distillation of the nitrobenzene in 

 a current of steam, was purified by repeated crystallisation from glacial acetic 

 acid. It consisted of yellow, prismatic, nodular crystals, which melted at 

 242-243° C. It was identical with the trinitro bodies formed by the action 

 of nitric acid on phenyl- 2-naphthylnitrosamine in acetic acid solution, and of 

 nitric and nitrous acids on phenyl-aceto-2-naphthalide. 



5. 1 -Mtro-Phenyl-2-Naphth yl mine. 



l-Nitro-phenyl-2-naphthylamine was prepared by Goldberg's method from 

 a mixture of 10 grams of l-nitro-2-naphthylamine, 6 c.c, of bromobenzene ami 

 6 c.c. of nitrobenzene with potassium carbonate, copper-dust, and potassium 

 iodide by heating to 150-160 ? C. for ten hours. After removal of the nitro- 

 benzene by distillation in steam, the residue was crystallised from hot alcohol, 



R.J.A. PROC, VOL. XXXIV, SEOT. B. 2.1 | 



