566 
added again and once more the solution gave a quantity of the 
same substance. On adding water to the filtrate this at first remained 
clear, but when about 150 c.c. had been added, a red substance 
precipitated. By the addition of more water, some more of this 
substance was obtained, while at last by neutralisation with soda a 
small quantity of the original product separated. 
The red substance melted at 103° and appeared to be the already 
known 2.5-dinitro-dimethyl-p-toluidine. The orange brown substance, 
fairly soluble in boiling alcohol, melted at 87°. Seeing the analytical 
results [ supposed I had to do with the still unknown 2.3-dinitro- 
dimethyl-p-toluidine. This proved to be the case indeed, as by oxi. 
dation with ekromie acid it is converted into 2.3-dinitro-monomethyl- 
p-toluidine, described by Pixnow *). 
I also converted the 2.3-dinitro-dimethyl-p-toluidine into the 2.3- 
dinitro-tolyl-methyl-nitrosamine, by dissolving it in nitric acid (D 1.20) 
and by slowly adding sodium nitrite. The nitrosamine precipitated, 
which on being boiled with acetic acid changed into the 2.3-dinitro- 
methyl-p-toluidine melting at 159°. 
If the 2.3-dinitro-dimethyl-p-toluidine is boiled for some time with 
ten parts of nitric acid (D. 1.49), then on pouring it out into water 
the already known 2.3.5 trinitro-4-tolyl-methyl-nitramine (m. p. 157°) 
precipitates. 
As the 2.3-dinitro-dimethyl-p-toluidine contained two nitro-groups 
in ortho-position, [ thought it might be of some interest to try to 
substitute one of them by interaction of ammonia and of different 
amines. For in this way, the ortho-position of the nitro-groups might 
be defined in another way than had been done by Pinnow (l.c); 
at the same time might appear the degree of mobility of that nitro- 
group which was to be substituted. 
It was to be expected, that the substitution of the nitro-group 
would not be easy. Sommer *) had studied the action of ammonia 
and of different amines —- aliphatic as well as aromatic — on 
2:3.5-trinitro-methyl-p-toluidine and on the nitrosamine and nitra- 
mine derived from it and he had experienced that it is true that the 
nitro-group was substituted, whilst methylamine als) acted on the 
nitramino-group, but that it was necessary in case of ammonia, 
methyl- and dimethyl-amine to work at 100° under pressure. 
Therefore I heated 0.5 gram of 2.3 dinitro-dimethyl-p-toluidine 
with 5 ee. of aleohol and 5 ¢.c. of ammonia (D. 0.91) for some 
1) J. p. Chem. 62, 505 (1900). 
2, J. p. Chem. 67, 513 (1908). 
