280 Dr. W. Ramsay on Picoline and its Derivatives, 



evaporation in a vacuum crystals of a brownish colour were 

 deposited, which deliquesced very rapidly on exposure to air* 

 After they had stood for some weeks over sulphuric acid, 

 the chlorine was estimated. 



I. 0-1700 grm. gave 0*1620 of Ag Cl= 22'42 per cent, of 

 chlorine. 



II. 0-1070 grm. gave 0-1038 of AgCl = 22'13 per cent, of 

 chlorine. 



Theory for C 6 H 7 N . C 2 H 3 CI, 22*83 per cent. 



When dissolved in water, picoline hydrochloride and free 

 acetic acid were formed. 



The benzoyl chloride was obtained in a similar manner and 

 possessed similar properties. It was not analyzed. 



It may perhaps not be uninteresting if I give an account 

 of some attempts made to decompose picoline, all of which, 

 with one exception, led to negative results. 



Picoline is not decomposed by potash in any form. Its 

 vapour may be passed over fused caustic potash, or it may be 

 boiled for a month with alcoholic potash, or it may be heated 

 for some days to 250° with alcoholic potash, without under- 

 going the slightest decomposition. This clearly proves that 

 it has not the nature of a cyanide or of a carbamine. 



It is not decomposed by a cherry-red heat, even in presence 

 of lead peroxide or of lime. It may be distilled through a 

 red-hot gun-barrel ten or twelve times without any deposition 

 of carbon, and the picoline which distils over has not even 

 a yellow colour. 



It is not attacked, at the temperature of boiling sulphuric 

 acid, by sulphuric acid, nor by a mixture of strong nitric and 

 sulphuric acids. 



When picoline nitrate is heated to about 200°, a violent de- 

 composition ensues ; red fumes are copiously evolved, and the 

 reaction goes on of its own accord. Unchanged picoline distils 

 over, mixed with oxides of nitrogen and carbonic anhydride 

 in large quantity : the presence of the latter gas was proved 

 by its precipitating an ammoniacal solution of calcium chloride. 

 Thorough decomposition takes place ; for nothing but picoline 

 nitrate is left in the retort ; and if distilled to dryness, a small 

 carbonaceous residue remains. Anderson states that pyridine 

 nitrate may be sublimed. Picoline is evidently more easily 

 oxidized than pyridine. 



Although I am acquainted with Alder Wright's and Dewar's 

 attempts, I believe it is premature to discuss a constitutional 

 formula for picoline. The probabilities appear to me to be 



