Processes in 'which Aniline is formed, 58S 



indigo, discovered, as is well known, the anthranilic acid, ha- 

 ving the formula 0,4 H^ NO4, which when distilled rapidly 

 yer se, or with lime, furnishes aniline and carbonic acid. 



C,4H7N04 + 2CaO, yieldingC,2H7N + 2CaO + 2COo. 



* , ' ^ , ' 



Anthranilic acid. Aniline. 



Investigations recently made, in quite another department 

 of organic chemistry, have presented us with two other bodies 

 whose composition agrees also with the formula of anthranilic 

 acid. 



Cahours once observed, during his researches upon the oil 

 of gaultheria, that the salicylate of oxide of methyle by the 

 action of ammonia is converted into salicylanide, a compound 

 isomeric with anthranilic acid. 



C,4H5 04+ NH2= C14H7NO4. 



■> ^ . ^ , . 



Salicylanide. Anthranilic acid. 



Deville * had beforehand discovered, as one of the pro- 

 ducts of the distillation of tolu balsam, a carbo-hydrogen pos- 

 sessing the greatest similarity with Faraday^s tri-carburet of 

 hydrogen (benzin-beir/.ole), which he called det2Zoe7ie ; and for 

 which Berzeliusf afterwards proposed the name toliiine. This 

 body, which according to Deville's analysis is represented by 

 the formula Cj4 Hg, when heated with fuming nitric acid, loses, 

 similarly to beuzin, one equivalent of hydrogen, which is re- 

 placed by the elements of peroxide of nitrogen ; the resulting 

 compound is protonitrobenzoetie, — Laurent's nitrobenzoenase 

 and Berzelius's nitrotoluid,— and possesses likewise the same 

 composition as anthranilic acid. 



Ci4 H3 + NO, giving C,4 H , NO4 + HO. 



Benzoene. Protonitrobenzoene. 



In relation to salicylamide, it is requisite to mention here 

 some researches antecedently performed by Gerhardl|. Before 

 this substance was discovered, the products of the distillation of 

 salicylate of oxide of ammonium were investigated by that che- 

 mist, with the view to obtain anthranilic acid, or at least aniline. 



C,4 H, O5 + NII4 O = C,4 H7 NO4 + 2HO. 



Salicylate of oxide of ammonium . Anthranilic acid. 

 A transformation of the above kind would have possessed 

 some similarity with the conversion of oxalate of ammonia into 



* Jn7iaL de Chim, et de Phijs., 3 ser. t. iii. p. 151, and Annal. der Chem, 

 und Pharm., bd. xliv. s. 304. 

 t Jahresbericht, xxii. s. 254. 

 i Jnnal. der Chem. und Pharm., bd. xlv. s. 24. 



