184 PROCEEDINGS OP THE AMERICAN ACADEMY. 



This ester must then, on boiling with water, be split by intra-molec- 

 ular oxidation into cyanisonitrosoacetamide, 



CN-C : NOH 

 I 

 HOC : NH, 



and into acetaldehyde, CHgCH : O. These considerations lead to the 

 conclusion that desoxyfulmiuuric acid must be identical with cyaniso- 

 nitrosoacetamide, and the following experiments, which have led to 

 a synthesis of this compound, prove that in fact both products are 

 absolutely identical. 



Cyanisonitrosoacetic ether, as well as cyanisonitrosoacetic acid, have 

 recently been obtained by Muller * from cyanacetic ether. I also 

 have made both these compounds in this way, and can confirm the 

 statements of Muller completely, except that the melting point of 

 cyanisonitrosoacetic ethylester was found to be 133° instead of 128°- 

 129°, when the substance is crystallized from benzene. Both com- 

 pounds were analyzed, and gave figures agreeing well with the theo- 

 retical ones. It is somewhat noteworthy that the ester melts higher 

 than the free cyanisonitrosoacetic acid. 



On heating cyanisonitrosoacetic ethylester (2 grams) in a sealed 

 tube with 10 c.cm. of alcoholic ammonia for four hours at 100°, a salt 

 separates out, on cooling, in yellow heavy nodules. It is filtered ofP, 

 well washed with alcohol, dissolved in hydrochloric acid, and extracted 

 with ether. After drying the ethereal solution with calcic chloride, 

 and concentrating, colorless heavy plates separate out. which, recrys- 

 tallized once more from ether, melt at 184° and are perfectly pure. 



0.1997 gram substance, dried over Hg'^Oi in a vacuum, gave 0.2325 



gram CO^ and 0.0520 gram H^O. 

 0.15i5 gram substance, gave 50.2 c.cm. Ng at 19° and 744 mra. 



Theory for C3H3N3O2. Found. 



C 31.86 31.75 



H 2.66 2.89 



N 37.17 37.27 



The substance crystallizes either in needles, or in heavy many- 

 sided flat crystals, and is identical in every respect with Seidel's 

 desoxyfulmiuuric acid. In order to be absolutely certain, this sub- 

 stance was made according to Seidel's directions, and compared in 

 every detail with the synthetic product ; no difference could be de- 



* Annales de Cliim. et de Phys., [7.], I. 504. 



