OF AROMATIC COMPOUNDS. 65 



an amido-naphthalene-sulphonic acid from a^oe^-nitro- 

 naphthalene-sulphonic acid. 



The following is true in all these cases where the 

 reduction is carried out in a concentrated sulphuric 

 acid solution: 



The nitro-groups are completely reduced to amido- 

 groups and a hydroxyl-group is taken up, always in a 

 para-position to one of the amido-groups. As in the 

 case of o-nitro-toluene sometimes also a sulpho-group 

 is taken up. p-nitro- toluene on electrolysis behaves 

 differently. Here the final product has the composi- 

 tion C 14 H u N,O a , and its formation is as follows: 



p-Amido-benzyl alcohol is formed from p-tolyl- 

 hydroxylamine (an intermediate product in the reduc- 

 tion of p-nitro-toluene) by molecular rearrangement, 



_ /CH 3 OH 



The amido-benzyl alcohol thus formed condenses 

 with one molecule of nitro-toluene (under the influ- 

 ence of the sulphuric acid), water being split off ' : 



u /CH,OH , r TT /CH, _ 

 ' H Cehl *\N0 3 



nitro-amino-o-benzyl-toluene, 

 C.H 4 - -CH -C 6 H 8 /3 + Ha0 



1 Chem. Ber., 26, 2810, 



