132 PROCEEDINGS OP THE AMERICAN ACADEMY 



C 6 H 5 N=C OH 



Pyruvic-anillde-phenylhydrazone, I 



CH 3 -ON-NHC 6 H 5 



If the above hydrazone-hydrate be heated a short time in alco- 

 holic or in acetic acid solution, or pyruvic anilide be treated in 

 hot alcoholic solution with one molecule of phenylhydrazine, the 

 phenylhydrazone of pyruvic anilide is formed quantitatively. Re- 

 crystallized twice from alcohol, it is obtained in colorless needles, 

 melting at 176°, and after drying at 110° it gave the following 

 results on analysis : — 



0.1508 gram substance gave 0.3930 gram C0 2 and 0.0819 gram 



H 2 0. 

 0.1736 gram substance gave 25.6 c.c. moist nitrogen at 17° and 



734 mm. 



Theory for C 15 H 15 N 3 0. Found. 



C 71.14 71.07 



H 5.93 6.03 



K 16.60 16.52 



The hydrazone is easily soluble in hot benzine, alcohol, and 

 acetic acid, and comes out on cooling in colorless needles. It is 

 insoluble in alkalies or in dilute acids. 



Phenylhydrazone of Pyruvic Acid, from Pyruvic Anilide. 



The proof that the above compounds are in reality derivatives ot 

 pyruvic acid is as follows. 3.5 grams pyruvic - anilide pheny lhydra- 

 zonehydrate were treated with 120 c.c. sodic hydrate (1:10), and 

 heated in an open dish on a water bath for half an hour. The 

 formation of aniline was recognized by the smell, chloride of lime 

 reaction, and by conversion into acetanilide. After cooling and 

 filtering, the solution is acidified with dilute hydrochloric acid. 

 A very bulky precipitate, consisting of yellow needles (2 grams) 

 was obtained. It was dissolved in soda, reprecipitated by acids, 

 and finally recrystallized from alcohol. The product obtained 

 melted with decomposition at 192°, and was identical in every 

 particular with a preparation which was made according to the 

 directions of E. Fischer and Jourdan.* 



* Ber. d. chem. Ges., XVI. 224, XVII. 578. 



