Manufacture of a New Compound Resulting from the Reaction of Methylphenyl Hydrazine and Salicylaldehyde.
Year: 1892

page_text: Date of Application, 25th Feb., 1892
Tomplete Specification Left, 23rd Nov., 1892-Accepted, 31st Dec., 1892
PROVISIONAL SPECIFICATION.
Manufacture of a New Compound Resulting from the Reaction of
Methylphenyl Hydrazine and Salicylaldehyde.
tt
I, Dr. ISRAEL Roos, of No. 7 Langestrasse Frankfurth on the Maine,
Germany, Chemist, do hereby declare the nature of this invention to be as
follows:-
+
This invention is based upon the reaction between a methylphenyl hydrazine and
salicylaldehyde. Proceeding from the inference that compounds wherein the
alcohol radical occupies a certain position in the atomic complex relatively to the
hydroxyl group would be characterised by certain therapeutic properties, I have
endeavoured to produce such a compound by the reaction of a methylphenyl-
hydrazine upon salicylaldehyde.
This experiment succeeded completely, inasmuch as the desired compound was
obtained by the means indicated, and on the other hand the compound obtained
was found to possess the therapeutical property anticipated, the toxical properties
of the mother substance being neutralised by the entrance of the alcohol radical.
The reaction is practically carried out as follows:
Equal molecules of unsymmetrical a-methylphenylhydrazine
-CH NN C-C¸H¸(OH)
CH(OH))
+ H₂O.
After cooling, a well crystallised reaction product is formed that can be
considered as salicylaldehyde a-methylphenylhydrazone and which I term
"antalgine." By recrystallising out of alcohol, the new body is obtained in a pure
state.
Instead of dissolving the a methylphenylhydrazine and the salicylaldehyde in
one and the same solvent such as methyl alcohol ethyl alcohol &c., each body can be
dissolved in a separate solvent. Thus for example the a methylphenylhydrazine
can be dissolved in dilute acid, and the salicylaldehyde in dilute alkali. On
combining the two solutions, salicylaldehyde-a-methylphenylhydrazone is formed
while the acid and the alkali combine to form a salt which can be separated from
the salicylaldehyde-a-methylphenylhydrazone, in the known manner by washing
and crystallisation.
Salicylaldehyde-a-methylphenylhydrazine is also formed if a methylphenyl-
hydrazine and salicylaldehyde, dissolved either alone or in one of the above-named
solvents, is heated for some time on a water bath.
The new compound in a pure state forms white crystals in the form of small
[D7]

page_text: laminæ, melts at 73° C., is insoluble in water but soluble in alcohol, ether, benzol,
ligroin &c. On boiling with concentrated hydrochloric acid it is decomposed.
This new compound is useful for therapeutical purposes.
Dated this.25th day of February 1892..
ABEL & IMRAY,
Agents for the Applicant.
COMPLETE SPECIFICATION.
Manufacture of a New Compound Resulting from the Reaction of
"Methylphenyl Hydrazine and Salicylaldehyde.
'
I; Dr. ISRAEL Roos, of No. 7 Langestrasse Frankfurth on the Main,
Germany, Chemist, do hereby declare the nature of this invention and in what
manner the same is to be performed to be particularly described and ascertained
in and by the following statement:―
This invention is based upon the reaction between a methylphenyl-hydrazine and
salicylaldehyde. Proceeding from the inference that compounds wherein the
alcoliol radical occupies a certain position in the atomic complex relatively to the
hydroxyl group, would be characterised by certain therapeutic properties, I have
endeavoured to produce such a compound by the reaction of a methylphenyl-
hydrazine upon salicylaldehyde.
This experiment succeeded completely, inasmuch as the desired compound was
obtained by the means indicated, and on the other hand the compound obtained:
was found to possess the therapeutical property anticipated, the toxical properties
of the inother substance being neutralised by the entrance of the alcohol radical.
The reaction is practically carried out as follows:-
Equal molecules of unsymmetrical a-methylhydrazine

page_text: Salicylaldehyde-a-methylphenylhydrazine is also formed if a methylphenyl-
hydrazine and salicylaldehyde, dissolved either alone or in one of the above named
solvents, is heated for some time on a water bath.
The new compound in a pure state which I term "antalgine" forms white
crystals in the form of small laminæ, melts at 73° C., is insoluble in water but
soluble in alcohol, ether, benzol, ligroin &c. On boiling with concentrated
hydrochloric acid it is decomposed. This new compound is useful for therapeutical
purposes.
Having now particularly described and ascertained the nature of my said inven-
tion and in what manner the same is to be performed I declare that what I
claim is :-
$6
"
1. A process for the production of a reaction-product termed antalgine
consisting in reacting with a methylphenylhydrazine upon salicylaldehyde, such
reaction being effected either directly or when the said substances are dissolved in
a solvent, and either with or without the application of heat, substantially as
described.
2. As a new manufacture, the reaction product, termed antalgine, resulting from
the reaction of a methylphenylhydrazine with salicylaldehyde as herein described,
such product consisting of white crystals that melt at about 73° centigrade, and
are insoluble in water but soluble in alcohol, ether, benzole, ligroin, and the like
substantially as described.
Dated this 18th day of Novembar 1902
ABEL & IMRAY,
Agents for the Applicant.