374 Decomposition of Aniline by Nitrous Acid. 



potash a salt crystallizing in bright yellow needles, very sparingly 

 soluble in water, of an intensely bitter taste and detonating when 

 heated, which was evidently nitrophenisate of potash. These 

 characteristic reactions show beyond a doubt, that the product of 

 this decomposition of aniline is nothing else than phenol or car- 

 bolic acid. 



The reaction may be represented by the following equation : 



1 eq. of aniline and 1 eq. of nitrous acid yield 1 eq. phenol, 2 of nitrogen, and 1 of water. 

 C 6 H 7 N + NH0 2 = C 6 H 6 4- N 2 + H 2 0. 



The same process applied to conine C 8 H, \ N should yield a 

 body having the composition of suberone C 3 H, 4 O, and cota- 

 mine C, a H, 3 N0 3 , would probably in like manner give phlo- 

 retine C I2 H l2 4 , or something isomeric with it. The exten- 

 sion of this process to the alkaloids, opens a wide field for inves- 

 tigation, and while it promises many new compounds, may ena- 

 ble us to fix with greater certainty than before, the composition of 

 some of those bodies, and thus disclose relations which will guide 

 us in obtaining artificially many of those important substances. 



As the intervention of nitric acid is objectionable from the dif- 

 ficulty of getting rid of it afterwards, and from its tendency to 

 change many organic substances, I thought, reasoning from the 

 ready decomposition of nitrite of ammonia, that the formation of 

 hyponitrites of the other alkaloids might obviate these objections 

 and yield satisfactory results. In pursuance of this idea, having 

 made a solution of nitrite of silver in boiling water, I added to 

 the still hot liquid, crystallized hydrochlorate of aniline in small 

 successive portions; a precipitation of chlorid of silver immedi- 

 ately appeared, followed after each addition by a violent efferv- 

 escence, which was due to the evolution of a colorless neutral 

 gas, without doubt nitrogen. Heat was then applied to the solu- 

 tion until the effervescence ceased, and the liquid which had 

 assumed a dark brown color and was covered with an oily film? 

 was treated with ether as in the previous experiment. The ethe- 

 rial solution left upon evaporation, a brownish, adhesive, semi- 

 fluid substance, which had a strong odor of castoreum, gave with 

 an acid the peculiar blue tint to pine wood, and in all its reac- 

 tions was identified with the product obtained by the action ot 

 nitric oxyd upon the nitrate of aniline. 



* An examination of the action of reducing agents upon the ether of nitrid or- 

 ganic acids, promises to yield some interesting bodies ot this class. I mixed an 



alcoholic solution ot nit robenzoic ether with sulphuric, arid, and di eaied thia With 

 zinc until water no loo r precipitated any ether from the solution; the alcohol 

 being removed by evap< ition at a gentle heat, caustic lime was added and the 



i;~„;j U.~J— 1 fit. .i nn .i-ii ,• _ i A, x- ._ .. l,A«nr nl 



agitated with ether. The 



taste 



The 



to examine farther the product, which appears to be a new alkaloid. 



