70 On the Transformation of Leucoline into Aniline. [Mar. 15, 



was slightly alkaline, and gave a platinum salt, of which 0*216 gram 

 yielded 0*0954 of platinum, equal to 44-16 per cent, of platinum, the 

 double chloride of platinum and ammonium requiring 44-23 per cent. 

 The mother-liquor yielded nothing apparently but the ammonium salt. 

 The acid on heating with potash-lime mainly undergoes the following 

 reaction : — 



C 9 H 9 N0 8 = C 6 H 7 N + C0 2 + H 2 + C 2 . 



When the crude mixture of potash salts resulting from the oxidation 

 is taken, instead of the pure acid, and distilled with soda-lime, there 

 appears to be associated with the aniline and pyrrols a small quantity of 

 a nitrile base having a lower boiling-point than leucoline. If the pure 

 potash salt is heated alone it fuses, aniline distils along with the vapour 

 of water, and a mixture of carbonate of potash and carbon is left. Thus 

 2C 9 H 8 KN0 3 = 2C 6 H 7 N + H 2 + K 2 C0 3 + C0 2 + C 4 . 



If the potash salt is fused with excess of potash, ammonia is evolved 

 and salicylic acid is found in solution. Probably anthranylic acid is the 

 first product, and this is subsequently changed into ammonia and sali- 

 cylic acid, viz. — 



(1) C 9 H 9 N0 3 + 3H 2 = C 7 H 7 N0 2 + 2C0 2 + H 8 . 



Leucolinic. Anthranylic. 



(2) C 7 H 7 N0 2 + H 2 = C 7 H 6 3 + KH 3 . 



Anthranylic. Salicylic. 

 A similar series of reactions take place when indigo is carefully treated 

 with fused potash. The formation of salicylic acid explains the origin 

 of the ammonia found associated with the aniline when the acid is heated 

 with potash-lime. 



A solution of the acid in glycerine, heated to the boiling-point of the 

 latter, gives a distillate of glycerine, aniline, and a substance in small 

 quantity having the characters of indol. No free carbon is separated in 

 this reaction. That indol or an isomeric body is likely to occur amongst 

 the products of decomposition appears from the following likely decom- 

 position : — 



C 9 H 9 N0 3 = C S H 7 N + H 2 + C0 2 . 



Leucolinic Acid. Indol ? 



This reaction is rendered probable from the relations of indol and ani- 

 line, indol being readily obtained from the reduction of isatine, and 

 isatine yielding aniline, carbonate of potash, and hydrogen on fusion 

 with potash. The relations of chinoline, leucoline, and indol will be fully 

 investigated in the second part of this paper, after I have had an oppor- 

 tunity of examining the isomeric cinchona bases. In the mean time it 

 may be remarked that pyrrol and pyridine have a similar relation to 

 indol and chinoline, thus — 



Pyrrol. Pyridine, Indol, Chinoline. 



