284 PROCEEDINGS OF THE AMERICAN ACADEMY 



also bromine seemed to be removed ; but as the product did not have 

 inviting properties, we have not attempted to isolate the oxime. If 

 the ketone is dissolved in chloroform, tlie solution mixed with bro- 

 mine, and allowed to stand at ordinary temperatures, hydrobromic 

 acid is given off in considerable quantity, and a new substance melting 

 at least 10° higher than the original is formed, which will be investi- 

 gated in this laboratory next term. It is a curious fact, that, if a solu- 

 tion of the ketone in carbonic disulphide instead of chloroform was 

 treated with bromine, no hydrobromic acid was given off, so far as we 

 could find. 



Anilidodinitrobenzyhnethylketone, CyH2( CgH-NH) (N02)2CH2COCH3. 



This substance is prepared easily by the action of aniline on the 

 bromdinitrobenzylmethylketone. The substances were mixed in the 

 proportion of one molecule of the ketone to two of the base, and the 

 mixture, which had a bright red color, warmed for 15 to 20 minutes 

 on the water bath. The product was then freed from the aniline 

 bromide and any slight excess of aniline by washing with water to 

 which a little hydrochloric acid was added, the residue, which con- 

 tained no bromine, purified by ciystallizatiou from hot alcohol till it 

 showed the constant melting point 131°, dried at 100°, and analyzed 

 with the following result : — 



0.1980 gr. of the substance gave 23.2 cc. of nitrogen at a tempera- 

 ture of 25° and a pressure of 771.2 mm. 



Calculated for 

 CbH2C6H5NH{NO,).,0H2COCH3. Found. 



Nitrogen 13.33 13.26 



Properties. — The anilidodinitrobenzylmethylketone forms, when 

 crystallized from alcohol, bright yellow groups of curving needles, 

 which look at first like two heads of palm trees cut off at the point 

 where the leaves grow out of the trunks, and put with the stumps 

 together. As more crystals are formed, the groups develop into 

 irregular chestnut burs. It melts at 131°; is essentially insoluble in 

 ligroine ; nearly insoluble in cold water, slightly soluble in hot, form- 

 ing a pale yellow solution ; slightly soluble in ether ; soluble in cold 

 ethyl or methyl alcohol, more freely in either of these solvents when 

 hot ; soluble in benzol, carbonic disulphide, or glacial acetic acid ; 

 freely soluble in chloroform or acetone. Alcohol is the best solvent 

 for obtaining crystals. Strong sulphuric acid dissolves it, forming a 

 brown solution. Strong nitric or hydrochloric acid dissolves it with 

 a yellow color, but it is very slightly soluble in hydrochloric acid. 



