106 Scientific Proceedings^ lloyai Dublin Society. 



JV^itro-methyl-bcnzene-diazo-amino-o- toluene CJI3 ■ NOo . Me . No . NH . CeH^ . Me. 



(5) (2) (1) (1) (2} 



7'6 grams of nitro-toluidine were dissolved by warming with 50 c.c. cone, 

 hydrochloric acid diluted with an equal volume of water. The solution was 

 quickly cooled in ice, and the requisite quantity of sodium nitrite solution 

 added. The diazo solution was rapidly filtered, diluted to 250 c.c, and excess 

 of sodium acetate added. 5'35 grams of o-toluidine were dissolved in 30 c.c. 

 cone, hydrochloric acid and 50 c.c. water ; the solution was diluted to 500 c.c, 

 and excess of sodium acetate added. This solution was then cooled and added 

 to the diazo solution previously prepared, when an orange yellow precipitate 

 separated gradually. The substance was filtered oft" after standing overnight 

 and well washed with water. The crude product melted at IDS'" C, but after 

 four crystallizations from alcohol the melting point rose to ISS'' C. The 

 substance so obtained consisted of needle-shaped crystals, which decomposed 

 on boiling with hydrochloric, sulphuric, and acetic acids, giving nitro-cresol 

 [OH : Me : NO, = 1:2:6], o-toluidine, and nitrogen, thus showing it to be 

 a diazo- amino compound. Again, on heating with hydrochloric acid and 

 j3-naphthol it yielded nitro-methyl-phenyl-azo-/3-naphthol m.pt. 204° C. ; it 

 was found that about 12°/^ of the diazo-amino product reacts in this manner, 

 the remainder yielding nitro-cresol, toluidine, and nitrogen. 

 Analysis : — 



•1500 gram gave 25-8 c.c. moist nitrogen at 12" C. and 772 mm. 

 % N = 20-86. 



CuHulSriOa requires 20-74. 

 The " diazo " nitrogen was estimated by the method of Mehner (Journ. 

 fiir Prakt. Cheniie [2], 63, 304). 



•3000 gram gave 23 c.c. moist nitrogen at 20° C. and 764 mm. 

 ^ diazo nitrogen = 10-76. 



CeH^NO., . Me . N : N . NH . CJiMe requires 10-37. 

 On concentration of the mother liquor from the crystallization of the 

 above compound a small quantity of reddish crystals separated. This was 

 picked out and crystallized from alcohol, m.pt. 144° C. Under the micro- 

 scope the crystals were seen to be cubic. The amount of the substance was 

 too small for analysis : it was probably the isomeric 4-amino-3 : 2'-dimethyl- 

 5 -nitro-azo-benzene. 



Nitro-methyl-bemene-diazo-amino-p-tolucne CcHsNO, . Me . Nj . NH . CeHi . Me. 



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



1-52 gram nitro-toluidine was dissolved in 4 c.c. cone, hydrochloric acid 

 and 50 c.c. water, cooled to 0°C., diazotized with the requisite quantity of 



