662 
The structure proofs which these investigators bring forward for 
their supposed isomer III, are, however, quite insufficient. It, therefore, 
remained: 1st to decide what isomer or what isomers arise by the 
side of I (about which there is no difference of opinion); 2"d to 
furnish a conclusive structure proof for this isomer or these isomers. 
In the first place we have now found that all three isomers are 
formed, I as chief product, If and III as bye-products. In this we 
have proceeded as follows: The erude reaction product is perfused 
with an excess of 4 N-alcoholic ammonia, + mol. NH, to 1 mol. 
dichlor-dinitro-benzene. After some stirring most of it goes into 
solution. It is then left standing for two days at the temperature 
NH, 
é 
NO. NNO, 2-6 - dinitro-4- 
Ye 
chloraniline, melting-point 145°, which is for the greater part depo- 
sited in fine needles and almost pure‘). After filtration the alcoholic 
fitrate is distilled; then a residue is left, which consists of the isomers 
II and III, but also contains a certain quantity of the above mentioned 
chlor-dinitraniline. This residue is washed with water to remove 
Am-nitrite, then dried, and dissolved in about 4 liter of benzene 
(when 1 mol. of reaction product was started from). This solution 
is shaken out a few times with 20 ec. concentrated sulphuric acid, 
by which means the chlordinitraniline is removed. This is the case 
when the sulphuric acid gives no further colour. 
Then the benzene is distilled off, after which a residue remains, 
consisting chiefly of the compounds II and III, as can be shown by treating 
it again with alcoholic ammonia, 100 cc. 4 N. NH, to 50 gr. mix- 
ture. Then the liquid is digested (temp. in the flask 80—85°) for 
24 hours on a waterbath at a reflux condenser, and ammonia gas 
is led in a few times to compensate the loss. Then the liquid is 
neutralized, the greater part of the alcohol is distilled off, and the 
rest is poured into water. Through treatment of the reaction pro- 
duet with sulphurie acid, as given above, 2 nitro-3-6-dichloraniline 
Cl Cl 
7 \NH, VON NO; 
goes into solution and 1-4-dichlor-2-5-dinitro NO! 
| 
JNO; NA 
Cl Cl 
benzene remains behind. 
of the room. Then I is converted into 
1) It contains still a certain quantity of the isomer III, from which it can be 
separated by sulphuric acid, see below. 
