198 



Professor Kolbe. 



[Mar. 12, 



Calculated for C 6 H 4 NH 2 ,COOH, 5'1 per cent. H, and 61-3 per 

 cent. C. 



The transformation of the isatoic acid into the hydrochloric- 

 anthranilic acid is complete, as given by the above equation, in which 

 the hydrochloric acid, as taking part in the reaction, must be in- 

 cluded. 



Tolerably concentrated sulphuric acid acts upon isatoic acid in 

 exactly the same way as hydrochloric acid does ; the product is the 

 sulphuric-anthranilic acid, which can in this way be easily got beau- 

 tifully crystallised in large quantities. The anthranilic acid separated 

 from it gave an analysis corresponding to its composition. 



Dilute nitric acid acts upon isatoic acid in a manner analogous to 

 the above two acids, while concentrated turns it into a nitro-deriva- 

 tive which is described below. 



Hydrochloric acid gas, acting upon the alcoholic solution of isatoic 

 acid, decomposes it in such a manner that carbonic acid escapes, 

 while the ethyl ether of anthranilic acid is formed. Hydrochloric acid 

 gas was led to saturation, with gradual warming, into alcohol hold- 

 ing finely-powdered isatoic acid in suspension ; the resulting clear 

 solution solidified, on cooling, to a mass of pale-yellow needles, which, 

 after washing with alcohol or, better, ether, were analysed. The 

 compound is hydrochloric -anthranilic ether : — 



C 6 H 4 NH 2 ,COOC 2 H 5 .HCl. 



0-2330 gram substance gave 0*4602 gram C0 2 (0*1255 gram C), 

 and 0-1298 gram H 2 (0*0144 gram H). 



Calculated for the formula 



C 9 H 12 N0 2 C1. Found. 



53 -60 p. c. C 53 -86 p. c. C. 



5*95 „ H 6*18 „ H. 



This compound is only slightly soluble in cold alcohol, and not at 

 all in ether. It melts at about 170°, and can be sublimed by cautious 

 heating, but not altogether without decomposition. When brought 

 in contact with water, hydrochloric-anthranilic ether is decomposed 

 into its constituents ; the oil which here separated out, and which after 

 washing with water and drying over chloride of calcium, was dis- 

 tilled, is the ethyl ether of anthranilic acid, a strongly refracting 

 liquid boiling at about 260°. 



Analysis — 



0*3233 gram substance gave 07737 gram C0 2 (0'2110 gram C), 

 and 0-1995 gram H 2 (0*0221 gram H). 



- 3999 gram substance gave at 15° and 754 mm. pressure 30*2 c.c. 

 N (0-3509 gram N"). 



