459 



We have decompot^ed the reaction pioducl with water accoidiiig 

 to Tschitschibabin's direction, dissolved it in ether, and distilled 

 it at a pressure of 15 m.m. The bulk went over at 104 — 125°, 

 and was almost pure anunopjridine in agreement with the records 

 of the investigatoi- mentioned. At 130—180° and 15 m.m. an oil 

 distilled, which soon gets a dark colour when exposed to the air. 

 After some time white crystals separated out of this oil. Recrjstallized 

 out of water these crystals became colourless, long needles melting 

 at 73°. This substance is the hydrate of y-y-dipyridyl, which has 

 already been described by Anderson. After drying in a vacuum 

 exsiccator we obtained the y-y-pyridyl itself, which melts at 112°. 

 We identified this substance by analysis and by oxidation with 

 potassium permanganate. We obtained white crystals melting at 

 307°, which agrees with the melting-point of iso-nicotinic acid. On 

 action of picric acid on y-y-dipyridyl, both dissolved in alcohol, 

 we obtained a picrate crystallizing in line yellow needles, and 

 melting at 252°. As appears from analysis this picrate contains 1 

 mol. of picric acid to 1 mol. of y-y-dipyridyl. With anhydrous acetic 

 acid and zinc dust the y-y-dipyridyl gave the intensive violet colour 

 reaction, which was lately described by Dimroth and Heene. 



There are still some more substances to be found in the oil that 

 distilling at J 30— 180° and 15 m.m. pressure. After the bulk of 

 the y-y-dipyridyl had been removed from this oil, we treated the 

 liquid with hydrochloric acid. Two chlorides were then obtained, 

 which both crystallized in white needles. After recrystallisation from 

 diluted hydrochloric acid one melted at 115—116°; the second 

 melted above 280°. The latter substance appeared to be the salt of 

 y-y-dipyridyl. 



We have liberated the base from the chloride of 115 — 116°, and 

 obtained white crystals melting at 94— 95°. This melting-point agrees 

 with the «-«-dipyridyl-amine (C6H4N.),NH, which was obtained by 

 Steinhausrr and Diepolder ^) from «-chloro pyridine and «-amino 

 pyridine by heating with barium oxide. 



The nitrogen percentage of our crystals, which melt at 94 — 95°, 

 agrees with the value calculated for dipyridyl amine. 



TscHiTSCHiBABiN says that this dipyridyl amine is formed through 

 the action of two molecules of pyridine on 1 mol. of sodium amide, 

 but does not yet describe the experiments from which this appears. 

 When speaking of the action of 1 mol. of pyridine on J mol of 

 sodium amide (the same way as we performed the reaction) Tschit- 



1) Journ. f. prakt. Ghem. 93, 393 (1916). 



