ACTION OF THE HALOGENS^ ETC. 165 



methyl group remains unchanged in contrast to what occurs iu the 

 reaction with orthotoluquinoline where the methyl group is split off. 

 The following chlorine bodies were obtained: a dichlorparatoluquino- 

 line, melting at 80° — 81°, and a trichlorparatoluquinoline, melting at 

 159°. These could easily be separated by means of hydrochloric acid 

 on account of their difference in basicity. 



In a former investigation Edinger' has shown that bromine can 

 easily be substituted into the quinoline molecule by means of SgBrg. 

 Glaus and Mliller^, and Glaus and Lang^ obtained by means of bro- 

 mine alone, in the case of orthotoluquinoline, products in which the 

 bromine was substituted in the side-chain. By the action of S^Br^ 

 upon paratoluquinoline a substitution product was here obtained, in 

 which the bromine entered the quinoline molecule itself. This mono- 

 bromparatoluquinoline melts at 84° — 85°. 



Juvalta* and Kupp^ have shown that iodine can easily be substi- 

 tuted into aromatic hydrocarbons by means of fuming sulphuric acid. 

 This method was used to obtain iodine substitution products, inas- 

 much as frequent attempts to introduce iodine into quinoline by 

 means of the iodide of sulphur have proven useless. By the use of 

 acid containing 50 per cent. SOg and the calculated amount of iodine, 

 splendid yields of a di-iodoparatoluquinoline melting at 135° were 

 obtained. In like manner a dibromparatoluquinoline melting at 

 185° can be made. 



EXPERIMENTAL PART. 



Action of the chlorides of sulphur upon paratoluquinoline. 



A. 

 Action of S2GI2 on the oil bath at 150°. 



Fifty grms. paratoluquinoline were mixed with one hundred 

 grms. S2CI2 in a flask immersed in ice. The mixture was then 



(^) Journal fur Prakt. Chemie, Band 51, 355. 



C) Freiburffer Dissertationen, 1897. 



(') Freiburger Dissertationen, 1898. 



(*) Friedlander, Fortschritte der Teerfarbenf abrikation, 2, 93. 



{•) Berliner Berichte. 29. 1625. 



