Chemistry. — ''The Action oj Sodiuniamide on Pyridine, and 

 some Properties of a-(iminopi/ridine" . By J. P. Wibaut 

 and Elisabeth Dingemansk. (Communicated by Prof. A. F. 

 Hollkman). 



(Communicated at the meeting of December 30, 1922). 



Through Tschitschibabin's ^) beautiful researches «-aminopjridine 

 has become easily accessible. This investigator found that sodium 

 amide acts on pyridine as follows : 



C,H,N + NaNH, = C.H^N.NHNa -f H,. 



On decomposition of the reaction product with water, aminopyridine 

 and sodium hydroxide is formed. 



As we required this substance as starting material for synthetic 

 investigations, we have applied the method of preparation found by 

 TscHiTSCHiBABiN. Though also in our experiments «-aminopyridine 

 was formed as chief product, we found othei- substances than the 

 Russian investigator among the by-products. 



We experienced that the action of sodium amide on pyridine can 

 take place in different ways, dependent on the nature of the sodium 

 amide preparation used. We have prepared sodium amide according 

 to Titherley's indication by the action of carefully dried ammonia 

 on melted sodium at 350 — 400° C. The preparation obtained was 

 a pure white, showed a crystalline fracture, and contained no free 

 sodium. This preparation did not react with pyridine. A preparation 

 prepared at 300°, reacted very slowly with pyridine. In this expe- 

 riment very little «-amino pyridine was however, formed; further 

 a little y-y-dipyridyl, and some other products, which we did not 

 examine. 



A sodium amide preparation of Kah1;Baum, which was pretty 

 impure, as it contained free sodium and also sodium hydroxide, 

 acted vigorously on pyridine, as Tschitsohibabin states. Another 

 preparation of Kahlbaum, which was apparently much purer, acted 

 in exactly tfie same way. A mol. of pyridine is diluted with toluene, 

 and this mixture is heated with a mol. of finely powdered sodium 

 amide at 120 — 125° for seven hours. 



1) Journal de la Société Physico-Chimique Russe, 46, 1216 (1914). 

 Ghem. Zenlral Blatt 1915. I. 1065. 



