461 



In many experiments we prepared some liundreds of grammes of 

 aniino pyridine; the i-eaction always proceeded as we described 

 above. We never observed a substance with a melting-point of 158°; 

 nor did we ever observe a diamino pyridine. 



Accordingly the action of sodium amide on pyridine can evidently 

 give rise to the formation of different substances. We liave not been 

 able to find out why with some sodium amide preparations amino 

 pyridine was not formed. Addition of small quantities of water or 

 free sodium had no influence on iliis. We also caused sodium to 

 act on a mixture of pyridine and toluene, both at the ordinary 

 temperature and at the temperature of boiling. In this case there 

 was formed a tough amorphous mass, insoluble in water and in 

 organic solvents, soluble in acids. By extraction with ether we could 

 isolate only a small quantity of y-r-dipyridyl. This result is in 

 accordance with the early experiments of Andkkson. 



The formation of the important quantities of y-y-dipyridyl in our 

 amidisation seems, therefore, not to be in connection with a possible 

 percentage of sodium in the sodium amide preparation used. 



As amino pyridine seems comparable with aniline, we examined 

 the action of oxidizers on this pyridine base. For so far as we know, 

 nothing is known about this. 



Bichromate and diluted sulphuric acid change a diluted solution 

 of amino pyridine onlj' slowly at ordinary temperature. When the 

 mixture is left standing for some days, the liquid gets dark. From 

 this solution an amorphous green substance is isolated, insoluble in 

 water, alcohol, and ether, soluble with emerald green colour in 

 diluted liydrochloric acid. On evaporation of the hydrochloric acid 

 an amorphous blue substance was left behind. At 90° the action 

 of sulphuric acid and bichromate on amino pyridine takes place 

 more violently ; and amorphous products are also formed. In these 

 experiments part of the amino pyridine however remained unchanged. 



The action of potassium bichromate in acid solution on this base 

 takes place much less rapidly than in case of aniline. 



The action of potassium permanganate proceeds in an entirely 

 different way. Amino pyridine is rapidly changed by permanganate 

 in acid solution; after a few minutes all the permanganate has 

 disappeared. When a diluted solution of amino pyridine is added 

 to a diluted permanganate solution containing soda, a slow action 

 takes place. When, however, first a neutral permanganate solution 

 is added to a diluted solution of amino pyridine, and then a few 

 drops of 107o sodium hydroxide, a change of colour is immediately 

 seen. When we siart from a 0.1 "/^ solution of amino pyridine, the 



