A NEW ORGANIC BASE FROM COAL-TAR. 135 
have here brought together in the form of a table, which does not pretend to any 
scientific arrangement, its sole object being to point out the remarkable relations 
of aniline and picoline to the group. 
Indigogene, . . ; . Cy.H, NO, Indine. 
Indigo, . . 6 . Cig H, NO, cod 
Isatine, : : : . C,H; NO, 
Anthranilic acid, - 5 . C,H, NO, Boe 
Salicylic acid, I : . Cy Hy Og (Re 
Nitrosalicylic acid, . i . Cy H; (NO,) O, | - 
Benzoic acid, : : . Cy HH, O, Salicylous acid. 
Nitrobenzoic acid, . ¢ . Cy H; (NO,) O, Nitrosalicylous acid. 
Chlorobenzoic acid, ; . CyH; ClO, Chlorosalicylous acid. 
Hydruret of benzoil, , . Cy, O, Benzoine. 
Benzonitril, . : ‘ . C,H N Azotide of Benzoil. 
Stilbene, 5 ; ; . CyH, ae 
Phenol, : : ; . Cy HH, Oo Rete 
Aniline, : : : . CyH,N Picoline. 
Tribromaniline, . : . C,H, Br, N Tribromopicoline ? 
Benzin, : ; 3 «| Gy i, ? 
Nitrobenzid, . , : . Cy H; (NO,) 
The facility with which aniline can be obtained by the decomposition of dif- 
ferent members of this group, renders it by no means impossible to anticipate the 
artificial production of picoline also. 
As we can start from benzoic acid, and convert it into benzin, benzin into 
nitrobenzid, and that finally into aniline by the action of sulphuretted hydrogen, 
it seems by no means improbable that salicylous acid, the isomeric of benzoic 
acid, may be made to undergo a similar series of changes, the final result of 
which would be the formation either of picoline, or of some other compound 
isomeric with it and aniline. In order to subject this hypothesis to the test of 
experiment, I mixed salicylous acid with equal weights of slaked lime and caustic 
baryta, and distilled in the oil bath, with the view of obtaining a substance which 
should be isomeric with benzin. The greater part of the salicylous acid, how- 
ever, passed over unchanged ; but by agitating with solution of potass, there was 
left undissolved an excessively minute quantity of a solid crystalline substance. 
Finding this mode of operating unsuccessful, I passed salicylous acid over spongy 
platinum heated to a very low red heat in a glass-tube. <A dark viscid oily fluid 
passed over into the recipient, of which the greater quantity dissolved in caustic 
potass, but left behind a larger quantity of the solid substance than was yielded 
by the first experiment. By distillation with water this substance passed into 
the receiver in the form of oily drops, which solidified on cooling, and formed a 
crystalline mass in which minute needles could be detected. It had a peculiar 
pleasant smell which resembled that of benzin; but the quantity which I ob- 
tained was much too minute to admit of its analysis, or of any attempt to con- 
vert it into picoline. 
* Geruarpr has observed (Precis de Chimie Organique, tom. ii., p. 21), that benzoic acid, when 
fused with hydrate of potass, evolves’ hydrogen, and gives the potass salt of a new acid. This may pos- 
sibly be isomeric with salicylic acid. 
VOL. XVI. PART II. 2™M 
