Manufacture of Beta-amido Crotonic Anilide, and of Beta-methyl- amido Crotonic Anilide.
Year: 1892

page_text: Date of Application, 5th Mar., 1892
Complete Specification Left, 5th Dec., 1892-Accepted, 7th Jan., 1893
PROVIDIUNAL SPECIFICATION.
[Communicated from abroad by THE FARBWERKE VORMALS MEISTER LUCIUS
AND BRUNING, of Hoechst 3/Main, in the Empire of Germany, Chemical
Manufacturers.]
Manufacture of Beta-amido Crotonic Anilide, and of Beta-methyl-
amido Crotonic Anilide.
I, OLIVER IMRAY of No. 28 Southampton Buildings, Chancery Lane in the
County of London, Chartered Patent Agent, do hereby declare the nature of this
invention to be as follows:-
My foreign correspondents have discovered that when acetylacetic anilide is
submitted to the action of ammonia or methylamine there is readily produced
beta-amido crotonic anilide or beta-methyl-amido crotonic anilide according to the
equations :
VIL
These anilides may be employed as raw materials for the production of very
valuable bodies having medicinal properties. Thus for example: pyrazolon
derivatives are obtained when they are oxidised under certain well defined
conditions.
The production of these bodies is carried out for example in the following
manner:
1 part by weight of acetyl-acetic anilide is dissolved in about 10 parts by weight
of water while heating, and gradually adding an excess of ammonia.
When the whole quantity of acetyl acetic anilide is dissolved, it is left to cool.
There then separates a substance of similar appearance to the acetylacetic anilide;
from analysis and its qualities it results that this substance is beta-amido-crotonic
anilide CH, C = CH CO NH CH. The body crystallizes from alcohol in the
NH,
-
form of white needles, in water it is almost insoluble, the melting point is 144°—
145° C.
Notwithstanding that its solution shows a neutral reaction, the body possesses
basic qualities, seeing that it is of easy solubility in hydrochloric acid.
The production of the beta-methylamido crotonic anilide is proceeded with in
quite analogous manner, substituting methylamine for the ammonia.
The beta-methylamido crotonic anilide has the melting point of 140-144° C.
is soluble with difficulty in water, casier in hot alcohol from which solvent it is
obtained in the form of white crystals. Its composition corresponds to the
formula CHN₂O.
14
Dated this 5th day of March 1892.
ABEL & IMRAY,
Agents for the Applicant.

page_text: COMPLETE SPECIFICATION.
Manufacture of Beta-amido Crotonic Anilide and of Beta-methyl-
amido Crotonic Anilide.
I, OLIVER IMRAY of No. 28 Southampton Buildings, Chancery Lane, in the
County of London, Chartered Patent Agent, 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 :-
My foreign correspondents have discovered that, when acetylacetic anilide is
submitted to the action of ammonia, or methylamine, there is readily produced
beta-amido crotonic anilide or beta-methyl-amido crotonic anilide according to the
equations :
CH, C = CH – CÓ NH C H + NH
=
H₂O + CH₂ C
=
CH – CO NHC H.
These anilides may be employed as raw materials for the production of very
valuable bodies having medicinal properties. Thus, for example, pyrazolon
derivatives are obtained when they are oxidized under certain well defined
conditions.
The production of these bodies is carried out, for example, in the following
manner.
1 part by weight of acetyl-acetic-anilide is dissolved in about 10 parts by weight
of water while heating and gradually adding an excess of ammonia.
When the whole quantity of acetyl acetic aniline is dissolved, it is left to cool.
There then separates a substance of appearance similar to the acetyl acetic anilide,
from analysis and its qualities it results that this substance is beta-amido-crotonic
anilide CH,C=CH-CO NH CH. The body crystallises from alcohol in the
NH₂
form of white needles; in water it is almost insoluble, the melting point is 144° to
145° C.
Notwithstanding that its solution shews a neutral reaction, the body possesses
basic qualities, secing that it is of easy solubility in hydrochloric acid.
The production of the beta-methylamido-crotonic anilide is effected in a quite
analogous manner, substituting methylamine for the ammonia.
The beta-methylamido crotonic anilide has a melting point of 140° to 144° C., is
soluble with difficulty in water, more easily in hot alcohol from which solvent it is
obtained in the form of white crystals. Its composition corresponds to the formula
C₁H₁N,O.
Having now particularly described and ascertained the nature of this inven-
tion and in what manner the same is to be performed, I declare that what I
claim is :-
1. The manufacture of beta amido crotonic aniline and of beta-methyl-amido
crotonic anilide by heating acetylacetic anilide in aqueous solution together with
ammonia or with methylamine.
2. Beta amido crotonic anilide and beta-methyl-amido-crotonic anilide produced.
in the above manner.
Dated this 1st day of December 1892.
ABEL & IMRAY,
Agents for the Applicant.