A NEW ORGANIC BASE FROM COAL-TAR. 133 



This salt diflfers in constitution from the aniline salt, which is represented by 

 the foiTOula 2 (Ci, H; N) + 3 Hg CI,; it taUies, however, perfectly with the compound 

 of chinoline and bichloride of mercury, which is Cis Hg N + Hg CI.. 



1 have not particularly examined the other compounds of picoline. 



Products of the Decomposition of Picoline. 



The small quantity of picoline at my disposal has hitherto prevented my ex- 

 amining particularly the products of its decomposition, a branch of the subject 

 which presents numerous points of interest. Such results, however, as I have 

 obtained, indicate a striking difference between the products afforded by it and 



aniline. 



When treated with nitric acid of specific gravity 1-5, picoline is immediately 

 dissolved, but without communicating to the fluid the fine iudigo-blue colour 

 which aniline produces under similar circumstances. On the application of heat 

 there is produced an extremely slow evolution of nitrous fumes, which contrasts 

 strikingly with the tumultuous action which aniline produces. After very long- 

 continued treatment with nitric acid, the fluid was evaporated to a very small 

 bulk, when it deposited large crystals in the form of rhomboidal tables. These 

 crystals, on being treated with potass, evolved picoline unchanged. The potass 

 solution was red, but it contained no carbazotic acid, at least no carbazotate of 

 potass was deposited on evaporation. 



An excess of bromine water added to picoline causes an immediate and abund- 

 ant precipitate of a reddish colour, which, on standing during the night, deposited 

 itself in the form of a transparent reddish oil. This substance is destitute of 

 basic properties, and is readily soluble in alcohol and ether, but not in water. 

 Aniline, when treated in the same manner, gives, as is well known, the bromani- 

 loid of Feitsche, which is solid, and crystallises in silky needles, fusible at 232°. 

 It seems probable that the oily fluid obtained from picoline may possess a con- 

 stitution similar to that of bromaniloid, in which case it would have the formula 

 Cio ^H+ Br,) N, and would receive the name of bromopicoloid. I had not enough 

 of it for analysis. 



The action of chlorine on picoline is remarkably analogous to that which it pro- 

 duces on anUine. When passed into anhydrous picoMne it is rapidly absorbed, 

 and colourless crystals, apparently of hydrochlorate of picoline, are deposited. 

 In a short time, however, the fluid becomes dark brown, and is finally converted 

 into a resin. This resin was mixed with water, and a current of chlorine passed 

 through it for some hoiirs. The fluid was then introduced into a retort, and dis- 

 tilled, a crystalline substance, passed over along with the water, and after all the 

 water had passed, another substance made its appearance, while a large quantity 

 of carbon was left in the retort. The quantity in which I obtained these sub- 

 stances was far too small to admit of their particular examination, but it appeared 



