130 PROCEEDINGS OF THE AMERICAN ACADEMY 



0.2739 gram substance dried over H 2 S0 4 in vacuum gave 20.8 c.c." 

 moist nitrogen at 24° and 756 mm. 



ory for C 9 H 9 N0 2 . Found. 



C 66.25 66.15 



H 5.52 5.59 



N 8.59' 8.47 



Pyruvic anilide dissolves in large amount in hot, but very little 

 in cold alcohol. It is insoluble in cold water, and about 7 grams 

 dissolve in a litre of boiling water. It crystallizes in long color- 

 less needles, and is also soluble in chloroform and ether (in the 

 latter case not easily). The substance is very stable towards warm 

 dilute hydrochloric and sulphuric acids, and long boiling there- 

 with causes little change. Caustic alkalies, as well as ammonia, 

 act upon it immediately; although insoluble in sodic carbonate, 

 and giving no reaction to test paper, pyruvic anilide dissolves in 

 the cold in two molecules dilute sodic hydrate. On acidifying, 

 however, not the original substance is obtained, but a product 

 comes down in white flakes melting at 196° • This is in all prob- 

 ability a polymeric pyruvic anilide, and the reaction which takes 

 place is the following. At first, the pyruvic anilide, just as the 

 mesoxanilide above, takes up a molecule of water, forming the 

 hydrate 



C 6 H 5 N=C OH 



CH 3 -Oqtt ' 



on acidifying, it loses water, and simultaneously with this, poly- 

 merization results. This becomes especially probable on compar- 

 ing the entirely similar behavior towards alkalies of oxanilethane 

 (page 125), 



C 6 H 5 N=C OH 

 I 

 R-O-CO 



and of pyruvic-o-toluide (page 145), 



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



I 

 CH 3 -CO 



Attempts to split pyruvic anilide into pyruvic acid (in alkaline 

 solutions) were unsuccessful, although in every case almost the 



