427 



pyrrole, in wliicli it is, tlierefore, assumed tliat the pyridine imclens 

 is united at tlie « C atom of the pyrrole nucleus. 



In how far this assumption is justified, will be discussed afler- 

 Avards. The preparation of these sid)staMces did not offer any special 

 difficulty; oil (he other haiiil, the coinersion of C (pyi'idyl) pyrrole 

 (11) into the methyl derivative, nicotyrine (111), was difficult to realize: 



^\ II II 



HC 



N 



CH 

 III. 



N 

 CH, 



CH 

 HC,^\c- 



HC 



N 



H.C — CH, 



-C CH, 



CH 

 IV. 



N 

 CH, 



When it is tried to methylate the pyrrol derivative at the nitrogen 

 atom by treating the potassium-compound with methyl-iodide, there 

 is also a molecule of methyl iodide combined with the nitrogen 

 atom of the pyridine nucleus, so that the iodine methylate of nicot- 

 yrine is formed, from which afterwards methyl iodide must be 

 split otf. 



PiCTET and Rotschy') have obtained but very little of the nicot- 

 yrine by this method. For the coiitinualion of his experiments Pictet 

 has, therefore, made use of a iiicolyrine preparation which was 

 prepared by oxidation from iiicoline (IV) by Bi.au's method. 



A similar jirocedure is of course impossible in our case. In the 

 end PicTET and Rotschy have succeeded in reducing nicotyrine to 

 nicotine by an indirect way through making use of iodine and 

 bromine substitution products. 



Hence if this synthesis is repeated, starting from ft-amino-pyridine, 

 an isomer of the nicotine can be built up, in which the pyridine 

 nucleus is substituted at the «-place. 



As «-amino-pyridine is at present an easily accessible substance, 

 it seemed not im|)0ssible to obtain sufficient quantities of all the 

 intermediate products, so that it may also be expected that it will 

 be possible to prepare so much of the final product that its properties 

 can be properly studied. 



^ 2. The preparation of N-{u-pyridyl)-pyrroIe. 

 For the preparation of N-(«-pyridyl)-pyrrole we have heated 25 gr. 

 of «-amiiio-pyridiue with 28 gr. of mucic acid. First the salt of 



1) Ber. d. deutsch. chem. Ges. 37, 1225 (1904). 

 Proceedings Royal Acad. Amsterdam Vol. XXVI. 



28 



