324 PROCEEDINGS OP THE AMERICAN ACADEMY 



Although phenylhydrazine readily reacts upon mucoxybromic acid, 

 even in dilute solution, the flocculent product formed rapidly turns 

 brown, and we have not succeeded in obtaining it in a form fit for 

 analysis. Hydroxylamine also yielded no more satisfactory results, 

 although we tried the reaction under a variety of conditions. On the 

 other hand, the primary aromatic amines in neutral or acid solutions 

 gave beautifully crystalline products with the greatest readiness. An- 

 iline, parabromaniliue, para- and metauitrauiline, ortho- aud paratolui- 

 dine, all yielded similar products, but we have thus far studied in 

 detail the aniline compound alone. Urea likewise gives a crystalline 

 condensation product which has not yet been further investigated. 



Anilmucoxyhromic Acid. 

 When aniline chloride is added to a dilute solution of mucoxybromic 

 acid, the solution soon becomes yellow, and after a short time solidifies, 

 with the separation of finely felted, light yellow needles. A moderate 

 excess of free hydrochloric acid in no way interferes with the forma- 

 tion of the product, so that it may be most conveniently prepared by 

 dissolving baric mucoxybromate in a slight excess of dilute hydro- 

 chloric acid, and adding a molecule of aniline dissolved in hydrochloric 

 acid. The product was recrystallized from hot water, dried over sul- 

 phuric acid, and proved then to be anilmucoxyhromic acid, formed 

 according to the equation 



C,H3BrO, + C«H,NH, = C,H,Br03 . C,H,N + H,0. 



I. 0.2775 grm. substance gave 0.4540 grm. COj and 0.0790 grm. 



H^O. 

 II. 0.2602 grm. substance gave 0.1810 grm. AgBr. 



III. 0.2526 grm. substance gave 0.1764 grm. AgBr. 



IV. 0.5563 grm. substance gave 25.2 cc. of moist nitrogen at 19° and 



under a pressure of 748 mm. 



Found. 



n. ni. IV. 



29.61 29.73 



5.21 



The air-dried acid apparently contained one molecule of water, 

 which it lost rapidly over sulphuric acid, or when heated to 70°. 

 At 100° a slow decomposition appeared to take place. The loss 

 of crystal water was accompanied by a change of color to brilliant 

 yellow. 



