OF ARTS AND SCIENCES. 145 



is in this case very unstable, and cannot be distilled under 

 reduced pressure, but dissociates to a marked extent into the 

 constituents. 



On pouring the crude product (18 grams) into 130 c.c. of water, 

 cooling with running water, it becomes solid very soon. In this 

 case form-o-toluide is formed exclusively: 11 grams were obtained, 

 melting at 63°, and also confirmed by a complete analysis. The 

 imidechloride has therefore been decomposed according to the fol- 

 lowing equation : 



CI 



CH 3 -C 6 H 4 -N-C 



/ 



+ 2H 2 0=CH 3 C 6 H 4 N<£ H + HC1 + CH 3 COOH. 

 CH 3 -CO M 



This decomposition is not surprising when one considers that 

 pyruvic-anilidimidechloride is decomposed by alcohol in a similar 

 manner (p. 127); and although on treating this imidechloride with 

 water pyruvic anilide is the chief product (p. 129), formanilide is 

 also formed, but in slight amount only. 



The above crude pyruvic-o-toluideimidechloride can however be 

 converted in part into pyruvic-o-toluide by pouring it into a 

 large amount of water. The yield is small (about 15%), and form- 

 o-toluide is present in larger quantiy, and it was not found possible 

 to effect a separation of these two products in a simple manner. 

 A polymeric pyruvic-o-toluide could however be isolated as fol- 

 lows. The crude imidechloride was poured into a large amount of 

 water, and allowed to stand for an hour. The mixture, consisting 

 also of some isonitrile, was extracted with ether, and the ethereal 

 solution treated with dilute sodic hydrate. The alkaline solution 

 was thereupon again extracted with fresh ether. On acidifying 

 nothing separates out, but ether extracts a substance, which is very 

 soluble in water (melting point 62°, crystallizing in six-sided 

 plates). 



On drying the ethereal solution with calcic chloride, a flaky 

 substance all at once begins to separate out in large amount. 

 Recrystallized twice from alcohol, it was obtained in colorless 

 needles, melting at 177°. 



0.2032 gram substance, dried at 110°, gave 0.5079 gram C0 2 and 



0.1153 gram H 2 0. 

 0.2244 gram substance, dried at 110°, gave 15.5 c.c. moist nitrogen 



at 16° and 752 mm. 

 vol. xxvii. (n. a. xix.) 10 



