Dr. TV. Ramsay on Picoline and its Derivatives. 275 



sparingly soluble in water, and communicates to it the taste 

 of a hypochlorite ; it dissolves in alcohol, and in glacial acetic 

 acid, and is precipitated on addition of water. When distilled 

 with soda-lime, ammonia and hydrogen are evolved, and no 

 carbonaceous residue is left in the tube. As the chlorine 

 compound evolved a peculiar smell when distilled with water, 

 an attempt was made to obtain some decomposition-products 

 which might lead to a better knowledge of its constitution. 

 Ether extracted from the distillate a few oily drops having a 

 very pungent smell ; by far the greater part of the chlorine 

 compound turned to a resin, which yielded no promising re- 

 sults on attempted purification. This oil also is formed when 

 the chlorine compound is distilled with soda, but not appa- 

 rently in greater quantity. The chlorine compound is 

 reconverted into picoline hydrochloride by treatment with 

 tin and hydrochloric acid. 



Action of Bromine on Picoline. — "When bromine is added 

 to picoline or when picoline is exposed to the action of bromine 

 vapour, it is transformed into a dark brown resinous-looking 

 substance. If this product is distilled, pure picoline hydro- 

 bromide comes over. The products formed are probably 

 picoline hydrobromide, and an analogous compound to that 

 formed by the action of chlorine on picoline ; more bromine 

 adds on to the hydrobromide and forms a dibromide of that 

 salt ; and direct union also probably takes place between the 

 picoline and bromine, forming a compound which was obtained 

 in a pure state by treating picoline with a solution of bromine 

 in chloroform ; the chloroform was removed by evaporation 

 in vacuo. A substance which crystallized in small interlaced 

 needles was deposited. It had a faint smell of bromine, and 

 on analysis was found to have the formula C 6 H 7 N . Br 2 . 



0*2535 grm. of substance gave 0*3523 grm. of Ag Bl- 

 and 0*0048 grm. of Ag, together equal to 0*1534 grm. of 

 Br, or 60*51 percent. Theory demands 63*24 per cent. ; but 

 bromine was evidently lost on exposure to air. 



A similar compound was formed by acting on picoline with 

 a solution of iodine monochloride in chloroform : the liquid 

 grew warm, and a direct addition-product was formed. On 

 evaporation of the chloroform in a vacuum in presence of 

 caustic soda and sulphuric acid to prevent moisture, and to 

 absorb chlorine, long yellow needles were deposited. An 

 estimation of chlorine and iodine gave the following results : — 

 0*3044 grm. of substance gave 0*4488 grm. of Ag 01 + Ag I, 

 which on reduction yielded 0*2565 grm. of Ag. 



I = 49*83 per cent. 01 = 13*63 per cent. Theory for 

 C G H 7 N . IC1, 1 = 49*70 per cent, 01 = 13*89 per cent. 



T2 



