and Treatment of a Compound of Phenylhydrazine
Year: 1886

page_text: Date of Application, 11th Nov., 1886.
Complete Left, 28th July, 1887.
Complete Accepted, 6th Sept., 1887.
[Communicated from abroad by THE "SOCIETY. OF CHEMICAL INDUSTRY IN BASLE,"
of Basle, Switzerland, Manufacturers.]
facture and Treatment of a Compound of Phenylhydrazine
I, OLIVER IMRAY of No. 28 Southampton Buildings, Chancery Lane in the County
of Middlesex, Fellow of the Institute of Patent Agents do hereby declare the nature
of this invention to be as follows:-
In a Provisional Specification of this date is described the manufacture of the
ethylether of a new acid which has the formula C₁, H, N, O..
This invention relates to the production of a compound from Phenylhydrazine and
this ethylether, and to the conversion of this compound into Antipyrine by treating it
with Iodine Methyl under pressure.
.
As an example of the process for producing the compound 100 parts by weight of
the ether (CH, N, O₁) are powdered and mixed with 76 parts of pure Phenyl-
hydrazine and the mixture is heated on a water-bath. In the first instance, the mixture
dissolves, but very soon it solidifies with violent reaction and escape of alcoholic
vapours, and forms a slightly yellowish crystalline mass, which, washed with some
alcohol and dried, yields a substance that melts at 200° Centigrade.
Instead of thus bringing both substances into direct contact, the ether may be
first dissolved in boiling alcohol and then mixed with hydrazine. From the liquid,
which at first is quite clear, the compound separates in crystals or in the form of
crystalline powder. This new compound of which the formula is C, H, N, O, forms
crystals, which are of slightly yellowish or reddish hue, or a fine crystalline powder,
melts and becomes decomposed at 200° Centigrade and is with difficulty soluble in
pure water or alcohol. It is insoluble in Methylalcohol, Acetic ether, Ether, Chloro-
form, Bisulphide of Carbon, Ligroine, Benzole, or Toluole. In Amylic alcohol it
dissolves to some extent and separates from the solution as a fine crystalline flour.

page_text: Potash- and Soda-lyes and Carbonate of Soda, as well as mineral acids and acetic acid,
easily dissolve this compound and separate it into Methyloxy chinizine and Ethylene-
diamine. Also when the compound is heated beyond 200° Centigrade separation into
Methyloxy chinizine and Ethylenediamine takes place.
27
The compound, C, H, N. O₂, can be converted into Antipyrine by heating
100 parts by weight of it with 100 parts of Iodine Methyl and 200 parts of Methyl-
alcohol for about 12 hours at a temperature of 120° to 130° Centigrade. When the
volatile component parts are distilled off, the residue is mixed with soda-lye until an
alkaline reaction takes place. Antipyrine is thus liberated which can be obtained in a
pure state by heating it with Benzole, Alcohol or any other suitable solvent.
Dated this 11th day of November 1886.
ABEL & IMRAY,
Agents for the Applicant.

page_text: I, OLIVER IMRAY, of No. 28 Southampton Buildings, Chancery Lane, in the County
of Middlesex, Fellow of the Institute of Patent Agents 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 :-
In the Specification No. 14617 of 1886 is described the manufacture of the
ethylether of a new acid which has the formula C₁ H, N, O.
24
This invention relates to the production of a compound from Phenylhydrazine and
this ethylether, and to the conversion of this compound into Antipyrine by treating it
with Iodine methyl under pressure.
As an example of the process for producing the compound, 100 parts by weight of
the ether (CH, N, O,) are powdered and mixed with 76 parts of pure Phenyl-
hydrazine, and the mixture is heated on a water-bath. In the first instance, the mixture
dissolves, but very soon it solidifies with violent reaction and escape of alcoholic
vapours, and forms a slightly yellowish crystalline mass which, washed with some
alcohol and dried, yields a substance that melts at 200° Centigrade.
Instead of thus bringing both substances into direct contact, the ether may be first
dissolved in boiling alcohol and then mixed with hydrazine. From the liquid which
at first is quite clear, the compound separates in crystals or in the form of crystalline
powder. This new compound, of which the formula is C., H., N, O,, forms crystals,
which are of slightly yellowish or reddish hue, or a fine crystalline powder, melts and
becomes decomposed at 200° Centigrade and is with difficulty soluble in pure water
or alcohol. It is insoluble in Methylalcohol, Acetic ether, Ether, Chloroform,
Bisulphide of Carbon, Ligroine, Benzole, or Toluole. In Amylic alcohol it dissolves to
some extent and separates from the solution as a fine crystalline flour. Potash and
Soda lyes and Carbonate of Soda, as well as mineral acids, and acetic acid, easily
dissolve this compound and separate it into Methyloxy-chinizine and Ethylenediamine.
Also, when the compound is heated beyond 200° Centigrade, separation into
Methyloxy-chinizine and Ethylenediamine takes place.
The compound C, H, N, O, can be converted into Antipyrine by heating 100 parts
by weight of it with 100 parts of Iodine-Methyl, and 200 parts of Methylalcohol for
about 12 hours at a temperature of 120° to 130° Centigrade. When the volatile

page_text: component parts are distilled off, the residue is mixed with soda-lye until an alkaline
reaction takes place. Antipyrine is thus liberated which can be obtained in a pure
state by heating it with Benzole, Alcohol, or any other suitable solvent.
Having thus particularly described and ascertained the nature of this invention
and in what manner the same is to be performed I declare that what I claim is ;
1. The herein described manufacture of a compound of Phenylhydrazine with the
ethylether of a new acid.
2. The herein described process for treating the compound referred to in the
preceding claim, for production of Antipyrine.