OF ARTS AND SCIENCES. 131 



calculated amovmt of aniline was obtained. The conversion into 

 pyruvic acid was accomplished finally in a roundabout way, 

 namely, by means of phenylhydrazine. 



Pyruvic-anilide-phenylliydrazonehydrate, 



C 6 H 5 N=C OH 



CH 3 -C° H 



N NH-NHC 6 H 5 



On adding to a cold ethereal solution of pyruvic anilide one mole- 

 cule of phenylhydrazine, a voluminous white precipitate separates 

 out almost immediately in the form of needles. After filtering off, 

 washing well with ether, and drying a short time over sulphuric 

 acid in a vacuum, a perfectly pure preparation is obtained. 



I. 0.1522 gram substance gave 0.3738 gram CO, and 0.0896 

 gram H 2 0. 

 II. 0.1512 gram substance gave 0.3688 gram C0 2 and 0.0907 

 gram H 2 0. 

 I. 0.1516 gram substance gave 21 c.c. moist nitrogen at 18° 

 and 748 mm. 

 II. 0.1506 gram substance gave 20.5 c.c. moist nitrogen at 18° 

 and 744 mm. 



Theory for Found. 



Phenylhydrazine has thus simply added itself to pyruvic anilide, 

 just as in the case of mesoxanilide, as follows: 



C 6 H 5 N=C OH C 6 H 5 N=C OH 



I + H 2 NXHC 6 H 6 = 

 CH 3 -CO CH 3 -C 



OH 



X NHNHCcHj 



That the resulting substance is not a salt-like compound, but an 

 addition product, is certain, since alkalies do not split it into its 

 components. The hydrazonehydrate thus obtained loses on long 

 standing, or quickly at 70°, water going over into the hydrazone. 

 Heated quickly in a capillary tube it melts with gas evolution 

 (water) between 101°-105°, and then solidifies again, and melts on 

 further heating at about 160°. 



