338 



Transformation of Aromatic Monamines. [Jan. 24, 



I have therefore, in the first place, endeavoured to establish the gene- 

 rality of the reaction by treating toluidine in a similar manner. The 

 phenomena observed when a mixture of 1 molecule of toluidine with 1 

 molecule of oxalic acid is distilled, are perfectly analogous to those presented 

 by the corresponding experiment with aniline. It was not necessary for 

 the purposes of the investigation to trace step by step the several phases 

 of the complicated processes. The crude distillate, which contained 

 abundance of tolylformamide, was therefore immediately heated with 

 strong hydrochloric acid and submitted to distillation. The oily substance 

 which distilled over with the water, evolved ammonia on being boiled with 

 soda-solution, and the filtrate from the insoluble residue yielded, on addition 

 of hydrochloric acid, a crystaUine acid which combustion, as well as analysis 

 of the silver-salt, proved to be tolylic acid. Here also tolylformamide gave 

 rise to tolonitrile, from which tolylic acid subsequently was produced. 



. an,] CHO] 



jo, + 'I = ^tH, In + h,o + CO,, 



CHO] 



C,H, In = C^KN + HO, 

 H J 



C,H,N + 2H,0 = C.H^O, + H3 N. 



Several varieties of tolylic acid are known to exist, and it can scarcely 

 be doubted which of the isomeric modifications is formed in this case. As, 

 however, I intend to follow this reaction somewhat further, I shall not for 

 the present go deeper into the question. 



The experience collected in the phenyl- and tolyl-serles, as might have 

 been expected, has also been confirmed in the naphthyl- series. 



The investigation of the naphthaline group in this direction appeared 

 more particularly interesting. The idea naturally suggested itself of com- 

 pleting this group by taking advantage of the new reaction for the forma- 

 tion of a series of compounds, the existence of which had long been 

 pointed out by theory, but the preparation of which as yet, notwithstanding 

 repeated attempts, had not succeeded. 



Naphthaline, the most common product of the action of high tempera- 

 tures on organic bodies, has, singularly enough, not as yet been traced to 

 a simple reaction. It was not doubtful that the hydrocarbon would in 

 time be met with as the result of the splitting up of an acid, holding to it 

 a relation similar to that which obtains between benzoic acid and benzole. 



This acid, which is represented by the formula 



is in fact procurable by the action of oxalic acid on naphthylamine, the 

 monamine of naphthyl-series. I propose to give a detailed account of this 

 interesting compound and of its derivatives in a subsequent communication. 



