148 PROCEEDINGS OP THE AMERICAN ACADEMY 



Benzoylform ic-o-toluide Phenylhydrazonehydrate, 

 CH 3 -C 6 H 4 N=C OH 



si it rivJ-H- 



^ 6 w 5 ^ NHNHC6 h 5 



One molecule of plienylhydrazine is added to a lukewarm (30°) 

 very concentrated solution of benzoylforniic-o-toluide, and the mix- 

 ture cooled to 0°. 



A white crystalline granular precipitate — the hydrazonehydrate 

 — separates out, which was well washed, dried on a porous clay 

 plate and finally for two hours over H 2 S0 4 in a vacuum. 



0.1563 gram substance gave 0.4134 gram C0 2 and 0.0879 gram 



H 2 0. 

 0.1976 gram substance gave 20.6 c.c. moist nitrogen at 19° and 



749 mm. 



Theory for C 21 H 21 N 3 2 . Found. 



C 72.62 72.13 



H 6.05 6.25 



N 12.10 11.90 



Plienylhydrazine has thus simply added itself to the carbonyl 

 group present in benzoylformic-o-toluide, 



C 6 H 5 =CO C 6 H 5 C v 



I + H 2 NNHC 6 H 5 = I x NHNHC C H 6 . 



CH 3 -C 6 H 4 N=C OH CH 3 -C 6 H 4 -N=C OH 



That no salt-like compound is formed in this case is shown by 

 the fact that sodic hydrate does not split it into the components. 



The hydrazonehydrate loses water on standing, or very quickly 

 at 60°, and becomes yellow and sticky; also on heating much above 

 30° in solution it is converted into a yellow hydrazone, which was 

 not further investigated. 1.3 grams hydrazonehydrate were heated 

 gently in alcoholic solution with sodium ethylate (from 0.5 gram 

 sodium), and then the alcohol distilled off. After adding water 

 and extracting with ether, the alkaline solution was acidified with 

 hydrochloric acid, and a yellow bulky precipitate obtained. It was 

 filtered off, dissolved in soda, reprecipitated, and finally crystallized 

 from acetic acid. Yellow needles were obtained melting at 153°, 

 and identical in every respect with a product, benzoylformic acid 

 phenylhydrazone, 



