ON THE ACTION OF THE HALOGENS AND THE 



SULPHUR HALIDES UPON PARATOLU- 



QUINOLINE, 



John B. Ekeley* 



The action of sulphur and the chlorides of sulphur upon the 

 organic bases, quinoline, orthotoluquinoline, oxyquinoline, isoquino- 

 line, and acridine has been studied by Edinger and his pupils. It 

 has long been known that the introduction of sulphur into cyanogen 

 compounds robs these of their poisonous qualities by the formation 

 of the harmless sulphocyanides. In like manner the investigations 

 of Edinger', Edinger and Treupel', and Edinger and Arnold^ show 

 that sulphur has a similar effect upon the organic bases above men- 

 tioned. It became of interest to study the action of the chlorides of 

 sulphur upon paratoluquinoline, more especially because, in the 

 investigations of Edinger and his students, in the cases of quinoline 

 and orthotoluquinoline, difficulties were encountered in that, by the 

 elementary analysis, an amount of hydrogen was always found which 

 was too high. This could not be referred back to any impurities 

 which might have been in the compounds analyzed. By the action 

 of SjCl, upon quinoline a compound containing sulphur was obtained, 

 the sulphur of which was held in combination with unusual tenacity, 

 so much so, in fact, that the compound could be distilled over glowing 

 copper under diminished pressure without decomposition taking 

 place. For this reason and also from a determination of the molecular 

 weight by the lowering of the freezing point method, it was assumed 



(') Journal fur Prakt. Chemie, Band 54. 340; Band 56. 273. 

 (2) Miinchener Med. Wochenschrift. No. 21, 22, 39, 1900. 

 (») Journal fiir Prakt. Chemie, Band 64, 182, 471. 



*The author wishes to express his appreciation to Prof. Dr. Albert Edinger of the University 

 of Preiburgr in Baden, under whose direction this investigration was carried out. 



