568 
aleohol and some drops of cone sulphuric acid *), then 2.3.5-trinitro- 
ethvl-p-toluidine, a yellow compound (m.p. 150°), is formed. 
On nitrating diethyl-p-toluidine, dissolved in cone. sulphuric acid, 
with a quantity of nitric acid calculated for two nitro-groups and 
on afterwards pouring it out into four volumes of water, the tem- 
perature rising to about 50°, the red 2.5-dinitro-diethyl-p-toluidine is 
formed (m.p. 50°) the structure of which has been defined by 
ALFTHAN. However, if I poured it out into two volumes of water, 
the temperature now rising to 80°. a cloudiness with evolution of 
nitrous vapours sûddenly manifested itself. A light red crystalline 
mass was slowly formed. This mass was treated with hydrochloric 
acid (D. 1,19); part of it dissolved and by dilution a red precipitation, 
the 2.5-dinitro-ethyl-p-toluidine (m.p. 105°), was formed in this 
solution. 
That part which did not dissolve in hydrochloric acid was 
recrystallized from acetone and afterwards from aleohol and formed 
a light yellow compound, 2.5-dinitro-tolyl-ethyl-nitrosamine (m.p. 84°). 
I could prove that the nitro-groups of the last mentioned com- 
pounds really take the places 2 and 5 by nitrosating the 2.5-dinitro- 
diethyl-p-toluidine. 
On dissolving this substance in nitrie acid (D. 1.2) and slowly 
adding sodium nitrite the above described nitrosamine (m. p. 84°) 
precipitates, which changes by boiling with acetic acid into the red 
2.5-dinitro-ethyl-p-toluidine (m. p. 105°). 
CoH5 x Cols C,H; yNO Cals y H 
NO, a Le NO, EN NO A 
NS NO, eee NOx es NOs 
CHs m.p. 50° CH; m.p. 84° CH, m.p. 105° 
If the three above mentioned substances are boiled with nitric 
acid (D. 1.49), they change into the 2.3.5. trinitro-tolyl-ethyl-nitramine. 
Nitro-derivatives of ethyl-o-toluidine. 
I started from 4-nitro-ethyl-o-toluidine prepared by nitrating ethyl- 
o-toluidine in twenty times its weight of sulfuric acid. Like Hanrzscu *) 
I] obtained it in yellow crystals and not as Mac Can.um *) mentions 
in light red needles. 
The latter reduced the nitro-group and got from the diamine, 
which had been formed, a chrysoidine by means of diazobenzene 
1) Sommer, J. p. Chem. 67, 535 (1903). 
2) B. 48, 1673 (1910). 
*) J. Chem. Soc. 67, 246 (1895). 
aanne die adi 
