492 M. H. Bleibtreu on Cumarine. 



decide whether nitrocumaric acid can be obtained by careful 

 fusion with caustic alkalies, or directly from cumaric acid, 

 by proper treatment with nitric acid. 



The formation of this acid would have been of some inter- 

 est. The late investigations of Zinin have shown us that 

 acids of this class, under the influence of reducing agents, as 

 hydrosulphuric acid, &c, exchange 4 equivalents of oxygen 

 for 2 of hydrogen, or, to express it otherwise, 1 -equivalent of 

 hyponitric acid for 1 of amidogen. 



Whilst bases are thus formed from nitro-carbohydrogens, 

 the electro-negative character of the nitro-acids remains un- 

 changed. Benzoic acid, for example, treated in the above 

 manner, gives the following series : — 



Benzoic acid . . HO, C 14 H 5 3 



Nitrobe n zoic acid . HO,C 14 -l^x >O s 



Amidobenzoic acidH tj^ p J"^4\n 

 Benzamidic acid J UU ' U i 4 \AdJ Us 



Were it possible to form from cumaric acid a similar series : 



Cumaric acid . . HO, C 13 H 7 O s 



Nitrocumaric acid . HO, C 18 < ^T^k > O s 



Amidocumaric acid HO, C 18 -^ .§ f0 5 . 



it gave a hope of producing artificially hippuric acid, for 

 amidocumaric acid is, according to its formula, nothing but 

 hippuric acid : 



HO, C 18 {^*} 5 = HO, C 18 H 8 N0 5 . 



. , p * v • 



Amidocumaric acid. Hippuric acid. 



Whether or not such a relation exists must be decided by 

 further experiments, which I intend still to make in this direc- 

 tion. In the following I will briefly state some experiments 

 made partly with the same intention, and which as yet have 

 not led to decided results. 



It was not impossible that by the direct action of reducing 

 agents on nitrocumarine an amidocumarine could have been 

 formed, which by treatment with alkalies might have been 

 converted into the desired acid. For this purpose a quantity 

 of nitrocumarine was mixed with alcohol, into which ammo- 

 niacal gas was passed till the whole was dissolved, and then 

 submitted for a considerable time to a current of hydrosul- 

 phuric acid. 



