VIII. New compounds produced by the substitution of nitrogen for hydrogen

Abstract

In several previous notes I have called attention to a peculiar double acid which is formed by the action of nitrous acid upon amidobenzoic acid, C 14 H 14 N 2 O 4 + HNO 2 = C 14 H 11 N 3 O 4 + 2H 2 O, the constitution of which, as far as my experiments go, may be represented by the formula [C 7 (H 3 N 2 ')O] [C 7 (H 4 , H 2 N)O] } H 2 } O 2 . There are not less than three other compounds known which empirically may he represented by the same formula as amidobenzoic acid, viz. nitrotoluol, salicylamide, and anthranilic acid. The two former substances differ from amidobenzoic acid both physically and chemically in a marked manner; anthranilic acid, on the other hand, is so closely allied to the benzoic derivative, that special experiments were required to distinguish these two bodies. Gerland, when he submitted the two acids to Piria’s well-known reaction, observed that both are converted by nitrous acid into non-nitrogenated acids, which, although still isomeric, essentially differ in their properties; amidobenzoic acid being transformed into a new acid,— oxybenzoic acid, whilst anthranilic acid yields salicylic acid.