CH139433A - Process for the preparation of a basic derivative of a substituted quinoline carboxylic acid. - Google Patents
Process for the preparation of a basic derivative of a substituted quinoline carboxylic acid.Info
- Publication number
- CH139433A CH139433A CH139433DA CH139433A CH 139433 A CH139433 A CH 139433A CH 139433D A CH139433D A CH 139433DA CH 139433 A CH139433 A CH 139433A
- Authority
- CH
- Switzerland
- Prior art keywords
- preparation
- acid
- carboxylic acid
- basic derivative
- quinolinecarboxylic acid
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims description 3
- 238000002360 preparation method Methods 0.000 title claims description 3
- LOAUVZALPPNFOQ-UHFFFAOYSA-N quinaldic acid Chemical class C1=CC=CC2=NC(C(=O)O)=CC=C21 LOAUVZALPPNFOQ-UHFFFAOYSA-N 0.000 title claims 2
- 239000002253 acid Substances 0.000 claims description 7
- 238000009835 boiling Methods 0.000 claims description 4
- 239000003960 organic solvent Substances 0.000 claims description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 4
- 239000003795 chemical substances by application Substances 0.000 claims description 3
- HDCAZTXEZQWTIJ-UHFFFAOYSA-N n,n',n'-triethylethane-1,2-diamine Chemical compound CCNCCN(CC)CC HDCAZTXEZQWTIJ-UHFFFAOYSA-N 0.000 claims description 3
- 230000007935 neutral effect Effects 0.000 claims description 3
- 150000003839 salts Chemical class 0.000 claims description 3
- 150000007513 acids Chemical class 0.000 claims description 2
- 150000004820 halides Chemical class 0.000 claims description 2
- 230000001225 therapeutic effect Effects 0.000 claims description 2
- QHSDSDASKCLTPD-UHFFFAOYSA-N 2-ethoxyquinoline-4-carboxylic acid Chemical compound C1=CC=CC2=NC(OCC)=CC(C(O)=O)=C21 QHSDSDASKCLTPD-UHFFFAOYSA-N 0.000 claims 1
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 4
- 239000002585 base Substances 0.000 description 4
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- IKHGUXGNUITLKF-UHFFFAOYSA-N Acetaldehyde Chemical compound CC=O IKHGUXGNUITLKF-UHFFFAOYSA-N 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- 235000019441 ethanol Nutrition 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- NGNBDVOYPDDBFK-UHFFFAOYSA-N 2-[2,4-di(pentan-2-yl)phenoxy]acetyl chloride Chemical compound CCCC(C)C1=CC=C(OCC(Cl)=O)C(C(C)CCC)=C1 NGNBDVOYPDDBFK-UHFFFAOYSA-N 0.000 description 1
- ICNCOMYUODLTAI-UHFFFAOYSA-N 2-chloroquinoline-4-carboxylic acid Chemical compound C1=CC=C2C(C(=O)O)=CC(Cl)=NC2=C1 ICNCOMYUODLTAI-UHFFFAOYSA-N 0.000 description 1
- CJKRXEBLWJVYJD-UHFFFAOYSA-N N,N'-diethylethylenediamine Chemical compound CCNCCNCC CJKRXEBLWJVYJD-UHFFFAOYSA-N 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- 229910001854 alkali hydroxide Inorganic materials 0.000 description 1
- 150000008044 alkali metal hydroxides Chemical class 0.000 description 1
- 239000007859 condensation product Substances 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D215/00—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems
- C07D215/02—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom
- C07D215/16—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D215/48—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen
- C07D215/50—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen attached in position 4
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Quinoline Compounds (AREA)
Description
Verfahren zur Darstellung eines basischen Derivates einer substituierten Chinolinearbonsäure. Es wurde gefunden, dass man zu einem basischen Derivat einer substituierten Chinolinearbonsäure gelangt, wenn man auf Säurehalogenide der 2-Halogen-4-chinolincar- bonsäure Triäthyläthylendiamin einwirken lässt und das erhaltene 2-Halogen-4-chinolin- carbonsäure-triäthyläthylend'iamid mit alkali schen Athoxylierungsmitteln umsetzt.
Das 2-Äthogy-4-chinolincarbonsäure-tri- äthyläthylendiamid bildet ein hellgelbes @01 vom Siedepunkt 158-1.60' bei 0,02 mm Druck. Die Base ist in; organischen Lösungs mitteln leicht löslich. Mit Säuren gibt sie neu trale, in Wasser leicht lösliche Salze.
Die neue Verbindung soll zu therapeuti schen Zwecken Verwendung finden. <I>Beispiel:</I> .Zu einer Lösung von 1,5 Teilen Triä- thyläthylendiamin (farblose Base vom Sdp. <B>160</B> bis 1.65', dargestellt durch Reduktion des Kondensationsproduktes aus as. Diäthyl- äthylendiamin und Acetaldehyd vom Siede punkt 40 bei 7 mm Druck) in 4 Teilen 10 % iger Natronlauge lässt man unter Rüh ren und Kühlen eine benzolische Lösung von 2,
2 Teilen 2-Chlor-4-ehinolincarbonsäure- chlorid allmählich zufliessen. Nach beende ter Reaktion wird mit Wasser gewaschen und das Lösungsmittel abdestilliert. Das 2- Chlor-4-chinolincarbonsäure - triäthyläthy len- diamid bildet ein gelbliches 01 vom Siede punkt 165 bei etwa 0,015 mm Druck. In organischen Lösungsmitteln ist es leicht lös lich. Mit Säure gibt die Base neutrale, was serlösliche Salze.
15 Teile 2-Chlor-4-chino-Iinearbonsäure- triäthyläthylen.diamid werden mit einer Lö sung von 2 Teilen Natriumhydraxyd in 4thyla,lliahol gekocht. Hierauf wird der Äthylalkohol abdestilliert, der Rückstand in Äther aufgenommen und mit Wasser gewa schen. Nach Entfernung des Lösungsmittels verbleibt das .2-Äahogy-4-chix@olin@arbo@säure- triäthyläthylendia.mid als hellgelbes 01. Die Base lässt sich im Vakuum destillieren.
An Stelle einer Lösung von AlkaIihydro- xyd in Äthylalkohol können auch andere alkalische Ahoxylierungsmittel Verwendung finden, zum Beispiel Meta.lläthylate in orga nischen Lösungsmitteln.
Process for the preparation of a basic derivative of a substituted quinolinearboxylic acid. It has been found that a basic derivative of a substituted quinolinearboxylic acid is obtained if triethylethylenediamine is allowed to act on acid halides of 2-halo-4-quinolinecarboxylic acid and the 2-halo-4-quinolinecarboxylic acid-triäthyläthylend'iamid obtained with alkali between ethoxylating agents.
The 2-Äthogy-4-quinolinecarboxylic acid tri-ethylethylenediamide forms a light yellow @ 01 with a boiling point of 158-1.60 'at 0.02 mm pressure. The base is in; Easily soluble in organic solvents. With acids it gives neutral, easily soluble salts in water.
The new connection is intended to be used for therapeutic purposes. <I> Example: </I>. To a solution of 1.5 parts of triethylethylenediamine (colorless base with bp 160 to 1.65 ', produced by reducing the condensation product of as. Diethylethylenediamine and acetaldehyde with a boiling point of 40 at 7 mm pressure) in 4 parts of 10% sodium hydroxide solution, while stirring and cooling, a benzene solution of 2,
Gradually flow in 2 parts of 2-chloro-4-ehinolincarboxylic acid chloride. When the reaction has ended, the mixture is washed with water and the solvent is distilled off. The 2-chloro-4-quinolinecarboxylic acid - triäthyläthylen- diamid forms a yellowish oil with a boiling point of 165 at about 0.015 mm pressure. It is easily soluble in organic solvents. With acid, the base gives neutral, water-soluble salts.
15 parts of 2-chloro-4-quino-Iinearbonsäure- triäthyläthylen.diamid are boiled with a solution of 2 parts of sodium hydroxide in 4thyla, lliahol. The ethyl alcohol is then distilled off, the residue is taken up in ether and washed with water. After removing the solvent, the .2-Äahogy-4-chix @ olin @ arbo @ säure- triäthyläthylendia.mid remains as a light yellow 01. The base can be distilled in vacuo.
Instead of a solution of alkali hydroxide in ethyl alcohol, other alkaline aoxylating agents can also be used, for example Meta.lläthylate in organic solvents.
Claims (1)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH139433T | 1927-11-19 | ||
| CH137338T | 1931-12-21 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH139433A true CH139433A (en) | 1930-04-15 |
Family
ID=25712943
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH139433D CH139433A (en) | 1927-11-19 | 1927-11-19 | Process for the preparation of a basic derivative of a substituted quinoline carboxylic acid. |
Country Status (1)
| Country | Link |
|---|---|
| CH (1) | CH139433A (en) |
-
1927
- 1927-11-19 CH CH139433D patent/CH139433A/en unknown
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