( 644 ) 
but that this readily takes place with derivatives of methyl- 
aniline; for instance m.-nitro-methylaniline was readily converted 
into VAN ROMBURGH’s tetranitro-phenylmethylnitramine. Several 
observations have already been made as to the bromination and 
nitration of methylamine derivatives and it seemed of importance 
to further extend the same. 
VaugeL ') has shown that methylaniline readily yields a tribromo- 
derivative, while vaN Rompuren ”) has obtained trinitro-phenyl- 
methylnitramine by nitration of methylaniline. VAN ROMBURGH*) 
has also proved that if the o.- and p.-positions are occupied by a 
CH3-group only two NOs-groups are introduced. The same has 
been demonstrated by GRIMAUX en LEFÈVRE) for the group OCH. 
The object of my research was to ascertain the influence exer- 
cised on the further substitution by the occupation of ortho- and 
para-positions and also of the meta-positions of methyl and ethyl 
derivatives. The first substance examined was p.-nitro-methylaniline 
obtained by heating p.-chloronitrobenzene with methylamine in 
alcoholic solution for 4 hours at 160°. By treatment with nitric 
acid of sp. gr. 1.52 it was directly converted into trinitro-phenyl- 
methylnitramine. A treatment with 1 mol. of bromine in glacial 
acetic acid gave 2-bromo-4-nitro-methylaniline, m. p. 118°; with 2 
mols. of bromine 2.6-dibromo-4-nitro-methylamine, m.p. 113° is 
obtained. 
By the action of nitric acid the first compound gave 2-bromo- 
4.6-dinitro-phenylmethylnitramine. m.p. 125°, the last one gave 
2.6-dibromo-4-nitro-phenylmethylnitramine, m. p. 84°. 
o.-Nitro-methylaniline, obtained like the para-compound from 
o.-chloronitrobenzene is converted by the action of nitric acid into 
trinitro-phenylmethylnitramine. Bromine converts this substance 
first into 4-bromo-2-nitro-methylaniline, m.p. 101° and then into 
4-6-dibromo-2-nitro-methylaniline, m. p. 100°. Treatment with HNO; 
gives 4-bromo-2.6-nitro-phenylmethylnitramine, m. p. 109° and 
2-4-dibromo-6-nitro-phenylmethylnitramine, m.p. 90°. 
On treating oxyethyl-dinitrobenzonitrile (1.2.4.6) in alcoholic 
solution with methylamine or ethylamine the OC,H;-group is replaced 
by NHCH; or NHC,H;. By the action of nitric acid of sp. gr. 
1.52 on these substances, the hydrogen combined with the nitrogen 
is replaced by NO, and consequently the corresponding nitramines 
are formed. In the same way it was shown that when a Cl-atom 
1) Journ. pract. Chem. (2) 48. 315. 
2) Rec. 2. 108. 5) Rec. 3. 392. 4) C. R. 112. 727. 
