XI. A, 2 Williams: Chemistry of the Vitamines 57 



cotinic acid likewise failed to produce satisfactory yields. A 

 small percentage of a substance which from its solubilities ap- 

 peared to be carbomethoxy derivative was obtained. The body, 

 however, was so unstable as to make its isolation in a pure state 

 difficult. As the yield was very unpromising, this method was 

 abandoned. If, however, carbomethoxy derivatives could be ob- 

 tained the acid chlorides of which are soluble in some neutral 

 solvent, they would possess a great advantage. The greatest 

 difficulty encountered in working with the pyridine carboxy acids 

 and their derivatives is their slight solubility in all ordinary 

 solvents. 



An attempt to condense p-oxynicotinic acid with itself by 

 the use of fuming sulphuric acid resulted in a mixture of what 

 appeared to be sulphonated bodies which possessed no marked 

 curative properties. Phosphorus pentoxide gave better results. 



Oxynicotinic acid was intimately ground with an excess of 

 phosphorus pentoxide. The mass was quickly transferred to 

 a dry flask fitted with a calcium chloride tube and heated in 

 an oil bath to 150° for twelve hours. The mass gradually sof- 

 tened and was converted into a brown gum, which was taken 

 up in a small quantity of warm water. On cooling, some crys- 

 tals of oxynicotinic acid separated out together with a quantity 

 of an amorphous, rather flocculent precipitate. This was sepa- 

 rated and tested on three neuritic fowls, using a dose of 0.1 gram 

 per OS. Great improvement resulted in two cases and an ap- 

 parently complete cure in the third. 



In another experiment acetic anhydride was used as a con- 

 densing agent. Oxynicotinic acid was boiled with acetic an- 

 hydride under a reflux condenser for thirty minutes. On 

 cooling, a mass separated very similar to that obtained in the 

 previous experiment. Three neuritic fowls were each given 

 by mouth 0.1 gram of this substance. Considerable improve- 

 ment followed in all cases, but the effect seemed less promising 

 than that of the previous preparation. 



