434 



The diffidilties experienced bj Pictet and Crépieiix when tliey 

 endeavoured to realize (he reaction, were already pointed ont in 

 the introduction. We met wilii the same difficulties in onr case. 

 Tiie potassium compound of the pyritlyl pyrrole naelting at 90° was 

 heated witii an excess of methyl iodide in a sealed tube at 100° for 

 three hours. The reaction product was fieed from supertluous excess 

 of methyl iodide and solved in water. On evaporation of tlie aqueous 

 solution crystals wei'e separated, while potassium iodide was present 

 in the nH)llier li([uor. These crystals were purified by recrystallisation 

 from a small quantity of water. Yellow-brown crystals were obtained, 

 melting at 186^. Analysis gave 8.95 for the nitrogen percentage, 

 and 42,55 for the iodine percentage. Calculated for CiiH,,N,I : 

 Nitrogen 9,34 V„, iodine 42.30'/.. 



This substance is, therefore, the iodine methylate of C («-pyridy^- 

 N-methyl-pyrrole: (CH,I)N-C,H, .C.H.N.CH,. 



.lust as in Pictet and Crépieüx' ex|)eriraents not only was the 

 nitrogen atom of the pyrrole nucleus methylated, but also a molecule 

 of methyl iodide had combined with the nitrogen atom of the 

 pyiidine-nucleus. 



This iodine methylate is easily soluble in water, sparingly in 

 alcohol, very liltle soluble in the other usual organic solvents. 



In order to split off the group C'H,I out of this compound, we 

 have followed the method which Pictet and Rotschy ') already 

 applied, i.e. heating with quick lime. 



The jodine-methylate was mixed with quick lime, and slowly 

 heated in a retort. Soon a liquid distilled over, which was received 

 in ether, in order to separate it from a little of the unchanged 

 methyl iodide compound, which had also been distilled over in a 

 small quantity. After evaporation of the ethereal solution there was 

 left a light yellow liquid; we have converted this base into the 

 picrate, which melted at 143° after a double recrystallisation from 

 alcohol, We found 18.19 for the nitrogen percentage of this sub- 

 stance, while 18.09 "/„ of nitrogen is calculated for the raonopicrate 

 of C («-py ridyl)-N-raethyl-pyrrole, 



We have, accordingly, very probably obtained the required methyl 

 derivative, which must, therefoie, be an isomer of nicotyrine. 



it seems, however, possible to carry out the methylation of the 

 C («-pyridyD pyrrole in such a way that the C («-pyridyl) N- 

 methyl-pyrrole is obtained without the necessity of following the 

 indirect way over the iodine methylate. 



1) L. c. 



