THE DECOMPOSITION OF NITROTOLUYLIC ACID. 
45 
These numbers furnish the following - per-centages of carbon and hydrogen: — 
I. II. 
Carbon .... 53 - 55 53'69 
Hydrogen. . . . 466 461 
The formula of nitrotoluylamide, C 16 
o 2 , nh 2 , 
or if we adopt the theory of 
Kolbe, that toluylic acid like benzoic acid is the oxide of a conjugate radical 
(C 14 H 7 )~C 2 
requires 
Carbon 53’33 
Hydrogen .... 4'44 
Properties . — Nitrotoluylamide is in its properties exactly analogous to nitrobenza- 
mide, from which it differs in composition by (C 2 H 2 ), the constant ascending or 
descending term of these organic series. It is very sparingly soluble in cold water, 
more so in hot ; but very soluble in alcohol, ether, and pyroxylic spirit. Its alcoholic 
solution crystallizes spontaneously in long, brilliant, yellow needles. Its fusing-point 
is about 245°Fahr. ; that of nitrobenzamide was determined by Chancel to be under 
212°; when heated with a concentrated solution of potash, it is converted into nitro- 
toluylate of that base. 
By the process above described for procuring this substance, it can only be ob- 
tained in very limited quantities, and the process is by no means unattended with 
danger, from the liability of the tube to burst under the great pressure to which it is 
exposed ; and whilst searching for some better method of procuring it in quantities 
sufficient to study the products of its decomposition, I became acquainted with the 
investigations of Chancel upon the nitro-compounds derived from benzoic acid*, 
and upon trying the method there proposed by him for the preparation of nitroben- 
zamide, I succeeded, after many fruitless trials, in obtaining the new amide in con- 
siderable quantities. The purified ethyl compound was dissolved in ordinary spirits 
of wine, and aqueous ammonia added until a precipitate began to form : the solution 
was transferred to a stout green glass bottle, and the stopper being well-secured, it 
was plunged into a water-bath and kept for several days at a temperature of about 
140° Fahr. The action proceeded very slowly; with about 15 grammes of ether it 
was usually completed in eight or ten days. The liquid, from being nearly colourless, 
was now of a deep yellow colour, and no precipitation took place on the addition of 
a large quantity of water. The ammoniacal alcohol was distilled off, and the residual 
crystalline mass redissolved in weak alcohol and boiled with animal charcoal ; from 
the filtered solution pure nitrotoluylamide separated in crystals of remarkable size and 
brilliancy. 
The formation of nitrotoluylamide by the action of ammonia on nitrotoluvlate of 
* Laurent and Gerhardt, C. R., 1849, 177, Annual Rep. Prog. Chem. vol. iii. part 1. p. 223. 
