Leonako and Browne — Some Deruativcs of Nilrotohiidine. 107 



sodium nitrite solution, the whole filtered, and excess of sodium acetate added. 

 The clear solution was added slowly to a solution of 1'07 gram j3-toluidine in 

 •4 c.c. cone, hydrochloric acid and 200 c.c. water containing excess of sodium 

 acetate. A yellow substance gradually separated, which was filtered off after 

 standing overnight. Twice crystallized from alcohol, the crystals melted with 

 decomposition at 131° C. It proved on examination to be a diazo amino com- 

 pound, decomposing on treatment with acids into nitro-cresol,^-toluidine, and 

 nitrogen. 



Analysis : — 



■1500 gram gave 25-8 c.c. moist nitrogen at 14-5° C. and 767 mm. 



% Nitrogen = 20-50. 

 CuHuNiOj requires 20-74. 

 Diazo nitrogen : — 



•oOOO grams gave 27-8 c.c. moist niti'Ogen at 20° C. and 767 mm. 



y^ Diazo nitrogen 10 '33. 

 CsHsNOo . Me . N ; N . NH . C^Hi . Me requires 10-37. 



A itro-mdliyl-diazo-aminohenzene-p-sulphonic acid 



CeHs . NOo . Me . N, . NH . CeH , SO3H. 



(5) (2) (1) (1) (4) 



■g-'o-tli molecule of nitro-o-toluidine dissolved in 75 c.c. of 10 °/„ sulphuric 

 acid and cooled to 0° C. was diazotized by -g-Vth niol. of sodium nitrite. The 

 solution was then added with constant stirring to a solution of c-Vth mol. of 

 sulphanilic acid in 100 c.c. of a solution containing -o-Vth mol. of sodium 

 hydroxide. 



Afler a short time a yellow amorphous substance separated, which, after 

 washing and drying in vacuo, melted at 129"^ C. with decomposition. It im 

 insoluble in water, alcohol, ether, and benzene in the cold, and only slightly 

 ■soluble on heating. When warmed with acids it decomposes with evolution 

 ■of nitrogen, showing it to be a diazo-amino compound. 

 Analysis : — 



•3000 gram gave 43-2 cc. moist nitrogen at 16° C. and 752 mm. 



% nitrogen = 16-71. 

 OisHioNiSOa requires 16-67. 

 Diazo nitrogen : — 



-3000 gram gave 21 c.c. moist nitrogen at 17° C. and 761 mm. 



7o diazo nitrogen =8-19. 

 CeH, . NO, . Me . N : N . NH . CeH.SOaH requires 8-33. 



