286 PROCEEDINGS OF THE AMERICAN ACADEMY 



turned yellow and turbid. It seems to be nearly or quite insoluble 

 in ether, and is insoluble in benzol. 



Anilidodinitrobenzyhnethylketonehydrazone, 

 C 6 H 2 (C 6 H fi NH)(N0 2 ) 2 CH 3 C(N 2 HC 6 H 5 )CH 8 . 



Tbis substance was made by warming for 20-30 minutes on the 

 water bath in an open dish a mixture of anilidodinitrobenzylmethyl- 

 ketone with phenylhydrazine in the proportion of one molecule of the 

 former to about one and a half of the latter, so as to have a decided 

 excess of the hydrazine. At the end of this time the mixture had 

 changed from yellow to dark carmine red, and solidified to a tarry 

 mass, which was crystallized once or twice from alcohol to bring it 

 into a finely divided state, and washed with water containing a little 

 hydrochloric acid till the excess of phenylhydrazine had been re- 

 moved, after which it was boiled with alcohol on the water bath, and 

 while boiling enough benzol added cautiously to effect the solution ; 

 the mixture was then boiled for about a minute, when upon cooling 

 crystals were deposited, and this crystallization was continued until 

 the substance showed the constant melting point 140°, when it was 

 dried at 100°, and analyzed with the following result: — 



0.2177 gr. of the substance gave 32.5 c.c. of nitrogen at a tempera- 

 ture of 22° and a pressure of 763 mm. 



Calculated for 

 C 6 H 2 (C 6 H 6 NH)(N0 2 ) 2 CH 2 C(N 2 HC 6 H 5 )CH 3 . Found. 



Nitrogen 17.28 16.97 



o 



Properties. — The hydrazone crystallizes well in reddish brown 

 scales, resembling strongly in general appearance the officinal ferric 

 citrate. The scales often reach a diameter of 3 to 4 millimeters. 

 Under the microscope plates were observed which seemed to belong 

 to the monoclinic system, but with these were very irregular forms, 

 often serrated on one or both sides, or irregularly diamond-shaped 

 with re-entering angles, usually either grouped in radiating masses, or 

 in crowded branching collections of thick needles. It melts at 140°, 

 but, as it seems to be slightly decomposed by crystallization, it was 

 difficult to determine the melting point with perfect exactness. It is 

 essentially insoluble in ligroine or cold water ; very slightly soluble in 

 boiling water or in ether; slightly soluble in cold alcohol, more solu- 

 ble, but still not freely, in hot; more soluble in methyl than in ethyl 

 alcohol ; slightly soluble in cold glacial acetic acid, freely in hot ; sol- 

 uble in cold benzol or carbonic disulphide, freely soluble in these sol- 



