ON ISOMERIC NAPHTHALENE DERIVATIVES. 267 
to reduce the keto-compound ; experiments made by Mr. Rich show that it 
is impossible to use it in reducing the nitro-keto derivates prepared from— 
Cl Cl 
OH neon OH 
and 
Br Cl 
The formation of the corresponding nitro-derivatives—in which the 
a-atom of chlorine is displaced from the nitro-keto-compound—amay, how- 
ever, be readily effected by means of hydrogen iodide, and the method 
appears to be of general application. 
With the object of ultimately preparing 2:5 chloro-/3-naphthol, 
attempts were made to ethylate 
NO, 
OH 
Cl 
But great difficulty was experienced, the yield being most unsatisfactory ; 
yet the allied compound 
Br 
is ethylated with the greatest ease. The case is apparently another illus- 
tration of the inhibiting effect of contiguous ortho groups to which Victor 
Meyer has called attention so frequently. 
In seeking to remove the atom of halogen in the a-position in the 
derivatives of /3-naphthol containing halogens,1l-chloro--and 1 : 3 dichloro- 
B-naphthol were heated with sodium as well as potassium sulphite in the 
hope of obtaining a-sulphonic acids ; the desired change was effected in 
the case of the mono- but not in that of the di-chloro-compound. 
Experiments carried out by Mr. Davis have led to the discovery of a 
simple means of converting 1 : 3’ dibromo into 3’ bromo-/-naphthol (m.p. 
127°), consisting in the mere digestion of the dibromo-compound with a solu- 
tion of hydrogen iodide ; but, again, in this case, we have hitherto failed in 
extending the use of the method to other derivatives containing halogens. 
With the object of ascertaining whether amido-/3-ethoxynaphthalene 
NH, 
OEt 
resembles either a-naphthylamine or (-naphthol, Mr. Davis has subjected 
its acetyl derivative to the action of bromine ; the results show that the 
amido group is apparently without influence, the behaviour being that of 
a derivative of 3-naphthol in which position 1 is occupied. 
