594 



V. " On New Nitrogenous Derivatives of the Phenyl- and Ben- 

 zoyl-Series." By P. GRIESS, Esq. Communicated by Dr. 

 HOFMANN. Received December 9, 1858. 



Piria's important discovery that the action of nitrous acid upon 

 asparagin gives rise to the formation of malic acid, has led to a very 

 general application of this agent in the study of nitrogenous sub- 

 stances. The results obtained have been almost always analogous 

 to those produced by Piria ; the reaction may be illustrated by the 

 following examples : 



6) " } O 4 . 



Malic acid. 

 O. 



Phenylamine. Phenol. 



The plan hitherto adopted consisted in submitting the aqueous 

 solution of the nitrogenous body directly to the action of nitrous 

 acid, or in dissolving the body in nitric acid, and passing into the 

 solution a current of binoxide of nitrogen. By employing alcoholic 

 and ethereal solutions, I have arrived at different results, establishing 

 a new mode of reaction ; of the facts which T have observed the fol- 

 lowing may be quoted as illustrations. 



Action of Nitrous Acid on Picramic Acid. Diazodinit rophenol. 



On passing a current of nitrous acid into an alcoholic solution of 

 picramic acid 



C 12 H 5 N 3 10 =C 12 ^(N6 4 )^0 2 . 



the red liquid assumes at once a yellow colour, and furnishes rapidly 

 a copious deposit of yellow crystals. No gas is evolved during the 

 reaction. The yellow crystals, purified by recrystallization from 

 alcohol, are found to contain 



C 12 H 2 N 4 10 , 



and are obviously formed according to the equation 



