An Anti-pyretic and Anti-neuralgic Chinolin Derivative and Processes for the Production of the same.
Year: 1892

page_text: Date of Application, 18th Feb., 1892
Complete Specification Left, 22nd Oct., 1892-Accepted, 3rd Dec., 1892
PROVISIONAL SPECIFICATION.
[Communicated from abroad by GUSTAV ADOLF DAHL, of the firm of Dahl and
Company, of Barmen, in the Kingdom of Prussia, Dye Stuff Manufacturers.]
An Anti-pyretic and Anti-neuralgic Chinolin Derivative and
Processes for the Production of the same.
I ADOLF BANG of Basinghall Street Leeds in the County of York Dye-stuff
Merchant, do hereby declare the nature of this invention to be as follows:-
The ortho-oxyaethyl-ana-amidochinolin previously described in the Specification
of Letters Patent No. 17493 under date 14th October 1891 or the hydrochloric
acid salt of the same furnish when boiled with benzoylchloride the o-oxyaethyl-a-
monobenzoylamidochinolin. This forms small yellow needles, which are very
difficultly soluble in water, more readily soluble in alcohol, and melt at 206° C.
The o-oxyaethyl-a-benzoylamidochinolin may moreover be readily and quite
smoothly produced by shaking the o-oxyaethyl-a-amidochinolin (suspended in water)
with an equal weight of benzoylchloride and the necessary quantity of soda ley to
fix the hydrochloric acid, which becomes set free. The excess of benzoylchloride
is removed by treatment with soda ley until the odour vanishes, then filter off, and
wash out the o-oxyaethyl-a-benzoylamidochinolin which remains behind.
The product thus obtained, shews at once a melting point of 200-202° C., and
with one recrystallization from alcohol is obtained pure, (melting point 206° C.).
The o-oxyaethyl-a-benzoylamidochinolin possesses anti-neuralgic and anti-pyretic
properties, and is intended for therapeutic application.
Example of the process of production.
The hydrochloric acid salt of the o-oxyaethyl-a-amidochinolin is boiled with
double its quantity of benzoylchloride, the mass from the reaction boiled with
water and then treated with ammonia, and the part remaining after filtration. is
recrystallized out with alcohol. The benzoyl product, at once pure, with melting
point 206° C. is the result.
If it is desired to proceed with the benzoylizing in the cold, the o-aethoxy-ana-
amidochinolin is stirred very fine with water, equal its own weight of benzoyl-
chloride added, and soda ley in quantity to fix the hydrochloric acid which becomes
free then gradually run in under active stirring, and then with occasional stirring
add sufficient soda ley until the odour of benzoylchloride vanishes, then filter
from the o-aethoxy-ana-benzoylamidochinolin and purify by recrystallizing out with
alcohol.
For instance the following proportions may be used.
100 gr. o-aethoxy-ana-amidochinolin, 500 gr. water and 100 gr. benzoylchloride
are mixed and 21.5 gr. soda ash (Na.OH) dissolved in 100 gr. water, then gradually
run in under active stirring.
Or one may dissolve the hydrochloric salt or tin double salt, as obtained according
to the Specification of Letters Patent No. 17493 of 1891, add soda ley until the
reaction is neutral and proceed according to the above just given quantities, noting
that 100 gr. o-aethoxy-ana-amidochinolin are equal to about 120 gr. of the hydro-
chloric salt or about 170 gr. of the tin double salt.
It will of course be understood that the above proportions are not exactly
binding, but may be somewhat varied from, and are given as a sufficiently practical
illustration of the method of carrying my invention sufficient for chemists versed
in this branch of chemistry.
This with day of 1809
J. CLARK JEFFERSON,
2, East Parade, Leeds, Agent for Applicant.

page_text: COMPLETE SPECIFICATION.
An Anti-pyretic and Anti-neuralgic Chinolin Derivative and
Processes for the Production of the same.
I ADOLF BANG of Basinghall Street Leeds in the County of York, Dye-stuff
Merchant, 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 :-
The ortho-oxyaethyl-ana-amidochinolin previously described in the Specification
of Letters Patent. No. 17493 under date 14th October 1891 or the hydrochloric
acid salt of the same, furnish when boiled with benzoyl chloride, the o-oxyaethyl-
a-monobenzoylamido chinolin. This forms small yellow needles, which are very
difficultly soluble in water, more readily soluble in alcohol, and melt at 206° C.
The o-oxyaethyl-ana-benzoylamido chinolin may moreover be readily and quite
easily produced by shaking the o-oxyaethyl-a-amidochinolin (suspended in water)
with an equal weight of benzoylchloride and the necessary quantity of soda ley to
fix the hydrochloric acid, which becomes set free. The excess of benzoylchloride
is removed by treatment with soda ley until the odour vanishes, then filter off,
and wash out the o-oxyaethyl-ana-benzoylamidochinolin, which remains behind.
The product thus obtained, shews at once a melting point of 200-202° C., and
with one recrystallization from alcohol is obtained pure, (melting point 206° C.).
The o-oxyaethyl-ana-benzoylamidochinolin possesses anti-neuralgic and anti-
pyretic properties, and is intended for therapeutic application.
Example of the processes for production.
The hydrochloric acid salt of the o-oxyaethyl-ana-amidochinolin is boiled with
double its quantity of benzoylchloride, the mass from the reaction boiled with
water and then treated with ammonia, and the part remaining after filtration is
recrystallized out with alcohol. The benzoyl-product, at once pure, with melting
point 206° C., is the result.
If it is desired to proceed with the benzoylizing in the cold, the o-oxyaethyl-ana-
amidochinolin is stirred very fine with water, equal its own weight of benzoyl-
chloride added and soda ley in quantity to fix the hydrochloric acid, which becomes
free; then gradually run in under active stirring, and then with occasional stirring
add sufficient caustic soda ley until the odour of benzoylchloride vanishes, then
filter from the o-aethoxy-ana-benzoylamidochinolin, and purify by recrystallizing
out with alcohol.
For example the following proportions may be used.
100 gr. o-aethoxy-ana-amidochinolin, 500 gr. water and 100 gr. benzoylchloride
are mixed and 21.5 gr. soda ash (NaHo) dissolved in 100 gr. water, then gradually
run in under active stirring.
Or one may dissolve the hydrochloric salt or tin double salt, as obtained
according to the Specification of Letters Patent No. 17493 of 1891, add soda
ley until the reaction is neutral, and proceed according to the above just given
quantities, noting that 100 gr. o-aethoxy-ana-amidochinolin are equal to about
120 gr. of the hydrochloric salt, or about 170 gr. of the tin double salt.
It will of course be understood that the above proportions are not exactly
binding, they may be somewhat varied from, and are given as a sufficiently
practical illustration of the method of carrying out my invention, sufficient for
chemists versed in this branch of chemistry.
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 :-
1st. The process or processes for the production of the o-oxyaethyl-ana-
benzoylamidochinolin either by means of the action of benzoylchloride on the

page_text: free base or its hydrochloric acid salt with heat, or suspended in water in the
cold in the presence of soda ley and purifying the raw product so obtained by
recrystallization out from alcohol or other solvents.
2nd. The ortho-oxyaethyl-ana-monobenzoylamidochinolin as above particularly
described.
3rd. The application of the ortho-oxyaethyl-ana-monobenzoylamidochinolin for
therapeutic purposes.
Dated this 21st dow of October 1899
J. CLARK JEFFERSON, Assoc. R.S.M.
2, East Parade, Leeds, Agent for Applicant.