220 PROCEEDINGS OF THE AMERICAN ACADEMY 



If, instead of sodium hydroxide, an aqueous solution of aniline is 

 added to the solution of pyromucamide in hromine water, a reddish 

 precipitate is produced. This substance is not stable. It melts at 

 about 78°, and appears to undergo decomposition when treated with 

 alcohol even in the cold. 



By substituting a saturated aqueous solution of phenyl hydrazine 

 for aniline, a brilliant red precipitate was obtained. The most 

 convenient method for preparing this substance is as follows. 

 Dissolve a weighed amount of pyromucamide in as small a quantity 

 of water as convenient ; add to this bromine, a few drops at a time, 

 shaking the flask and keeping it cool, until for each molecule of 

 pyromucamide two atoms of bromine have been added. The bro- 

 mine will be dissolved, and the solution will be almost colorless. 

 Filter if necessary, and add a large excess of a saturated solution 

 of phenyl hydrazine in water. Allow the mixture to stand for 

 some time, filter off the red precipitate formed, wash with water, 

 then with two or three small portions of alcohol, and lastly with 

 ether. Dry over sulphuric acid or in a steam-drying oven. The 

 yield is about 1.6 times the weight of the amide taken. The sub- 

 stance as thus obtained is bright red in color. It has no definite 

 melting point, but darkens in color between 150° and 160°. It is dis- 

 solved, and probably decomposed, by aqueous or alcoholic potassium 

 hydroxide, with a marked increase in the intensity of the red color. 

 It is very slightly soluble in chloroform, ether, and carbon disul- 

 phide, somewhat more readily in alcohol and acetone. Boiling 

 with alcohol and other solvents decomposes it, but it can be ob- 

 tained in small scale-like crystals by making a saturated solu- 

 tion at 50° in alcohol or acetone, and allowing it to cool and 

 evaporate spontaneously. The crystals are darker in color than 

 the amorphous material, and are quite brilliant. Qualitative tests 

 showed the absence of bromine. Analyses of the substance, both 

 in the crystalline and the amorphous state, were made with identical 

 results. 



The material used in analyses I. and II. was crystallized from 

 acetone, washed with ether and dried at 100°, while in analyses 

 III. and IV. an amorphous preparation was used which had been 

 washed successively with water, alcohol, and ether, and dried over 

 sulphuric acid. 



I. 0.3001 grm. substance gave 0.6684 grm. C0 2 and 0.1423 

 grm. H 2 0. 



II. 0.1005 grm. substance gave 17.2 c.c. of moist nitrogen at 

 23°. 5, and 754 mm. pressure. 



