IMPROVEMENTS IN THE PRODUCTION OF CERTAIN DERIVATIVES OF ALPHO OXYHYDRO-CHINOLINE AND OF BETA OXYHYDRO - CHINOLINE
Year: 1882

page_text: LETTERS PATENT to John Erskine, of 151 St. Vincent Street, Glasgow,
in the County of Lanark, North Britain, Solicitor, for an Invention of
"IMPROVEMENTS IN THE PRODUCTION OF CERTAIN DERIVATIVES OF ALPHO
OXYHYDRO-CHINOLINE AND OF BETA OXYHYDRO - CHINOLINE" the said
Invention is a Communication to him from abroad by the Farbwerke vorm:
Meister Lucius and Brüning, of Hoechst-am-Main in the Empire of Germany,
a Company carrying on business as Chemical Manufacturers
PROVISIONAL SPECIFICATION left by the said John Erskine at the Office
of the Commissioners of Patents on the 28th June 1882,
JOHN ERSKINE, of 151 St. Vincent Street, Glasgow, in the County of Lanark,
North Britain, Solicitor. "IMPROVEMENTS IN THE PRODUCTION OF CERTAIN
DERIVATIVES OF ALPHA OXYHYDRO-CHINOLINE AND OF BETA OXYHYDRO-CHINOLINE,"
[the said Invention is a Communication to him from abroad by the Farbwerke
vorm: Meister Lucius and Brüning, of Hoechst-am-Main in the Empire of
Germany, a Company carrying on business as Chemical Manufacturers.]
This Invention has for its object the preparation of the isomeric oxyhydro-
methyl-chinolines, and of the isomeric oxyhydro ethyl chinolines.
It is well known that two isomeric chinoline sulphonic acids are produced when
chinoline is treated with fuming sulphuric acid. According to the publications
of Bedall and Fischer, both isomers can be easily converted into the respective
oxyhydro-chinolines. (Berichte der Deutschen chem: Gesellschaft, 1881 p. 1366
& 1882 p. 683).
When the isomeric oxhydro-chinolines are treated with methyl-iodide or
etbyliodide they yield new compounds according to the following equations.—

page_text: imethyl or the Ethyl Iodide is used to react on the oxyhydro-chinoline. From the
hydriodide so obtained we obtain the corresponding oxyhydro-methyl or ethyl
chinoline (as the case may be) by precipitating the same from the hydriodide in
manner hereinafter mentioned.
For the purpose of explaining and illustrating the process, I shall now describe
the way in which I produce, for instance, the alpha oxyhydro ethyl chinoline,
that is to say :-
1 molecule of alpha oxyhydro chinoline is heated upon a water-bath with
1 molecule of ethyliodide until the reaction, which is violent at first, has come to a
standstill. From the crystalline mass thus obtained we extract the bydriodide of
oxyhydro ethyl chinoline by means of water, and from the aqueous solution of the
salt we precipitate the new base by means of caustic soda. It is afterwards
purified by recrystallization from alcohol. Without altering the result we can use
bromide or chloride of ethyl instead of the iodide of ethyl.
The isomeric oxyhydro methyl or ethyl chinolines (alpha and beta) can be used
in well known manner for the production of colouring matters by combining same
with aromatic diazo-compounds..

page_text: SPECIFICATION in pursuance of the conditions of the Letters Patent filed
by the said John Erskine in the Great Seal Patent Office on the
20th December 1882.
JOHN ERSKINE, of 151 St. Vincent Street, Glasgow, in the County of Lanark,
North Britain, Solicitor. "IMPROVEMENTS IN THE PRODUCTION OF CERTAIN
DERIVATIVES OF ALPHA OXYHYDRO-CHINOLINE AND OF BETA OXYHYDRO-CHINOLINE,*
the said Invention being a communication from abroad to me by the Farbwerke
vorm: Meister, Lucius, and Brüning, of Hoechst-am-Main, in the Empire of
Germany, a company carrying on business as Chemical Manufacturers.
This Invention has for its object the preparation of the isomeric oxyhydro-
methyl-chinolines, and of the isomeric oxyhydro ethyl chinolines.
It is well known that two isomeric chinoline sulphonic acids are produced when
chinoline is treated with fuming sulphuric acid. According to the publications of
Bedall and Fischer both isomers can be easily converted into the respective
oxyhydro-chinolines (Berichte der Deutschen chem: Gesellschaft, 1881 p. 1866
and 1882 p. 683).
When the isomeric oxyhydro-chinolines are treated with methyl-iodide or
ethyl-iodide, they vield new compounds according to the following equations :—
C, H, NO+CH,I=CH, NO + HL
C, H, NO + C, H,I=CH NO + HL
That is to say alpha or beta oxyhydro-chinoline plus methyl or ethyl iodide yields
hydriodide of oxyhydro-methyl or of oxyhydro-ethyl-chinoline according as the
methyl or the Ethyl Iodide is used to react on the oxyhydro-chinoline. From the
bydriodide so obtained we obtain the corresponding oxyhydro-methyl or ethyl
chinoline (as the case may be) by precipitating the same from the hydriodide in
manner hereinafter mentioned.
For the purpose of explaining and illustrating the process, the following
description is given of the way in which the communicator of the said Invention
produces, for instance, the alpha oxyhydro ethyl chinoline, that is to say :—
One molecule of alpha oxyhydro chinoline is heated upon a water bath with one
molecule of ethyliodide until the reaction which is violent at first, has come to a
stand-still. From the crystalline mass thus obtained we extract the hydriodide of
oxybydro-ethyl-chinoline by means of water, and from the aqueous solution of the
salt we precipitate the new base by means of caustic soda. It is afterwards
purified by recrystallization from alcohol. Without altering the result we can use
bromide or chloride of ethyl instead of the iodide of ethyl
The isomeric oxybydro methyl or ethyl chinolines (alpha and beta) can be used
in well known manner for the production of colouring matters by combining same
with aromatic diazo compounds.
Having now described and particularly ascertained the nature of the said
Invention and the system, mode, or manner in or under which the same is or
may be used or practically carried into effect, it is to be observed in conclusion
that what is considered to be novel and original and therefore claimed as the
Invention secured to the Inventor by the hereinbefore in part recited Letters
Patent is :-
The preparation of alpha oxyhydro-methyl chinoline and alpha oxyhydro-ethyl

page_text: chinoline and of beta oxyhydro-methyl chinoline and beta oxyhydro-ethyl
chinoline from alpha and from beta oxyhydro chinoline respectively in manner
herein before described, or in manner substantially the same.
In witness whereof I the said John Erskine have hereunto set my hand
and seal this Thirteenth day of December, in the year of Our Lord One
thousand eight hundred and eighty two.