
1905.] The Synthesis of a Substance allied to Adrenalin. 495 
substance, melting at 232° C. and is practically insoluble in water and neutral 
organic solvents. Most of the salts are readily soluble in water and give a 
beautifully crystalline compound when shaken with a strong solution of 
sodium bisulphite. The acetate forms a finely crystalline hydrazone on 
treatment with phenylhydrazine and a large excess of dilute acetic acid. 
Reduction of Methylamino-acetylcatechol—The reduction offered peculiar 
difficulties, since the majority of methods applicable for the reduction of 
ketones were inadmissible owing to the instability of these catechol deriva- 
tives in alkaline solution. However, it was found that reduction could be 
readily carried out electrolytically in acid solution using lead electrodes. 
The apparatus employed was similar to that devised by Tafel(11), and as 
it was important to keep the temperature of the liquid in the cathode 
compartment from rising above 16°, the cell was placed in a freezing mixture. 
One part of the base to be reduced is dissolved in the minimum quantity 
of dilute hydrochloric acid, or preferably the crystalline hydrochloride is 
taken, and the solution diluted with 15 parts of water. Fifteen parts of 
10-per-cent. sulphuric acid are then added to the solution, which is then 
placed in the cathode compartment. Owing to the sparing solubility of the 
sulphate of the base, it is advisable to add the sulphuric acid only just 
before commencing the reduction. The anode compartment is filled with 
10-per-cent. sulphuric acid. The reduction is not very rapid, as the time 
required for reducing 1 gramme of base in a small apparatus, using a current 
of 3 to 4 amperes, is about half an hour. After the reaction is completed the 
bulk of the sulphuric acid is removed by adding baryta, and the filtrate 
contains the sulphate of the new base. A large number of modifications 
of the above reaction have been tried, but as the products appear to be 
identical and the above process is the simplest, it is not proposed to give 
further details, but it may be mentioned that the reduction of the bi-sulphite 
compound of the base is particularly promising. The aqueous solutions of 
the salts of the new base, however obtained, may be concentrated in vacuo, 
but are rapidly decomposed if heated on the water-bath. 
On addition of ammonia, the free base is thrown out of solution as an 
amorphous greyish-white precipitate which very readily re-dissolves in acids. 
The base may be kept suspended in water for some little time without 
much change, but is so extraordinarily unstable in the dry condition that 
it has not yet been possible to obtain it in a fit condition for analysis. 
If one filters the base off as rapidly as possible and quickly removes adherent 
water by washing with dry alcohol and ether, it is found that the base has 
already undergone change, and is no longer completely soluble in dilute 
aqueous acids. This somewhat mysterious behaviour recalls that observed 
VOL. LXXVI.—B. 21 
