1869.] 



On the Action of Cyanogen on Anthranilic Acid. 



89 



V. " On the Action of Cyanogen on Anthranilic Acid." 

 By P. Griess, F.ft.S. Received June 29, 1869. 



Some time ago* I pointed out the action which takes place when 

 cyanogen gas is passed into an alcoholic solution of amidobenzoic acid. 

 The principal product of this reaction is, as I have shown, a yellow compound 

 of cyanogen and amidobenzoic acid of the formula C 7 H 5 (NH 2 )0 2 , 2CN, 

 which separates in large quantities as soon as the alcoholic solution of amido- 

 benzoic acid is nearly saturated with cyanogen. When anthranilic acid, a 

 body isomeric with amidobenzoic acid, is submitted under the same condition 

 to the same reagent, a totally different reaction takes place. In this case the 

 solution remains either perfectly clear, or only traces of a similar yellow com- 

 pound are precipitated. By allowing the alcoholic solution of anthranilic 

 acid, saturated with cyanogen, to stand for several days, the acid is almost 

 entirely converted into a new compound of the empirical formula C 10 H 10 N 2 O 2 ; 

 two other new compounds (an acid and an indifferent body) are at the 

 same time formed. It is worthy of remark that none of these compounds 

 are isomeric with any of the bodies which by the same process are formed 

 from amidobenzoic acid. Each of them belongs to a perfectly different type. 



I propose on this occasion to treat only of the principal product of the 

 reaction, viz. the compound C 10 H 10 N 2 0 2 . It is prepared in the following 

 manner. An alcoholic solution of anthranilic acid is saturated with cya- 

 nogen gas and left to stand for about eight days. The alcohol is then evapo- 

 rated at a low temperature, and the crystalline residue washed several times 

 with dilute solution of carbonate of ammonia, by which any traces of the 

 new acid (one of the by-products of the reaction) are removed. It is then 

 further purified by recrystallization from alcohol with the addition of a 

 little animal charcoal. The indifferent body already referred to, which 

 is very little soluble in alcohol, is thus separated. The new compound, 

 C 10 H 10 N 2 0 2 , is then obtained in the form of white acicular crystals, which 

 are very little soluble in boiling water, but dissolve readily in boiling 

 alcohol and ether. It fuses at 173°C, and can be distilled in small quan- 

 tities without undergoing decomposition. Its formation may be expressed 

 as follows : — 



C 7 H 7 N0 2 + 2CN + C 2 H 6 0= C 10 H 10 N 2 0 2 + CHN + H 2 O. 



Anthranilic Cyano- Alcohol. New compound. Hydro- Water, 

 acid. gen. cyanic 



acid. 



According to this equation, alcohol as well as anthranilic acid and cya- 

 nogen take place in the reaction. Confirmatory experiments which I have 

 made show that the compound in question is really an ether. 



Action of Hydrochloric Acid upon the Compound C 10 H 10 N 2 0 2 . — Ordi- 

 nary hydrochloric acid dissolves this body, and when cold does not act 

 upon it. On boiling, however, speedy decomposition sets in and a new 

 * Zeitschrift fur Chemie. New series, vol. iii. p. 533, and vol. iv. p. 389. 



