Ryan and Cullinank — Some Derivatives of SUlbene. 159 



lb consisted of yellow needles, wliich decomposed at 105" C, and gave a red 

 dye with alkaline (i-naplithol solution. After shaking the diazo-coniponnd 

 for twenty minutes, heat was applied for a short time by means of the 

 watei'-bath, Ihe mixture was then cooled, and water was added. The residue 

 obtained on filtering was extracted with ether, and on evaporation of the 

 solvent, colourless scales were obtained, melting at 124° C, which proved to 

 be stilbene. 



4:-Nitro-2-aminostilbe7ie. 



A warm solution of 20 grams of 2'4-dinitro3tilbene in 300 c.c. of glacial 

 acetic acid was vigorously stirred by means of a mechanical stirrer, and, at 

 the same time, was rapidly cooled with water. During the cooling process 

 the nitrostilbene was precipitated from solution in a finely-divided condition. 

 When a temperature of ;i5^ C. had been readied, a little more than the 

 calculated amount (for the reduction of one nitro-group) of a solution of 

 stannous chloride (prepared by passing hydrochloric acid gas into a mixture 

 of 60 grams of stannous chloride and 1.50 c c. of glacial acetic acid until the 

 tin salt had almost completely dissolved), at a temperature of 20° C, was 

 added gradually, while the stirring was continued. The temperature rose 

 slowly until in a few minutes the stilbene compound had gone almost 

 completely into solution. The product was allowed to cool, and to remain 

 overnight at the room temperature, when a dense yellow precipitate was 

 observed. The latter was separated by filtration from the mother liquor, 

 and decomposed with warm water. The red powder resulting was taken 

 up with hot alcohol, from which, on cooling, brick-red needles, melting at 

 142°-143° C, separated. The yield was i 1-12 grams. 



4:-JVitro-2-aviinostilbene is slightly soluble in light petroleum, but dissolves 

 readily in most organic solvents. 



2'4- IHaininodilhene. 



In this experiment somewhat more than the calculated amount of 

 stannous chloride was employed for the reduction of the two nitro-radicals 

 in 2-4-dinitrostilbene. On heating the mixture for a short time a dense 

 white precipitate was formed, and the reaction was then discontinued. The 

 deposit was separated from the mother-liquor, dissolved in water, and the 

 addition of concentrated ammonium hydroxide to the solution caused a white 

 solid to be thrown down. This was extracted with warm alcohol, from 

 which the diamine was obtained on cooling as white needles, melting at 

 119° C. It was slightly soluble in ether, moderately soluble in alcohol, 

 chloroform, or benzene, and readily soluble in glacial acetic acid or acelone. 



