CH139437A - 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
- CH139437A CH139437A CH139437DA CH139437A CH 139437 A CH139437 A CH 139437A CH 139437D A CH139437D A CH 139437DA CH 139437 A CH139437 A CH 139437A
- Authority
- CH
- Switzerland
- Prior art keywords
- iso
- carboxylic acid
- preparation
- acid
- basic derivative
- 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 description 3
- 239000002253 acid Substances 0.000 claims description 6
- 238000009835 boiling Methods 0.000 claims description 5
- 239000003960 organic solvent Substances 0.000 claims description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 4
- 150000007513 acids Chemical class 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
- -1 iso-amyloxy group Chemical group 0.000 claims description 2
- 230000001225 therapeutic effect Effects 0.000 claims description 2
- 150000004820 halides Chemical class 0.000 claims 1
- PHTQWCKDNZKARW-UHFFFAOYSA-N isoamylol Chemical compound CC(C)CCO PHTQWCKDNZKARW-UHFFFAOYSA-N 0.000 description 6
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- GRPQIEHRGUMHPJ-UHFFFAOYSA-N 3-ethylhexane-3,4-diamine Chemical compound CCC(N)C(N)(CC)CC GRPQIEHRGUMHPJ-UHFFFAOYSA-N 0.000 description 2
- 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
- 239000002904 solvent Substances 0.000 description 2
- QOEUTZHLPIWDBO-UHFFFAOYSA-N 2-(3-methylbutoxy)quinoline-4-carboxylic acid Chemical compound C1=CC=CC2=NC(OCCC(C)C)=CC(C(O)=O)=C21 QOEUTZHLPIWDBO-UHFFFAOYSA-N 0.000 description 1
- MFYSUUPKMDJYPF-UHFFFAOYSA-N 2-[(4-methyl-2-nitrophenyl)diazenyl]-3-oxo-n-phenylbutanamide Chemical compound C=1C=CC=CC=1NC(=O)C(C(=O)C)N=NC1=CC=C(C)C=C1[N+]([O-])=O MFYSUUPKMDJYPF-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
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 1
- CJKRXEBLWJVYJD-UHFFFAOYSA-N N,N'-diethylethylenediamine Chemical compound CCNCCNCC CJKRXEBLWJVYJD-UHFFFAOYSA-N 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 239000007859 condensation product Substances 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011734 sodium 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)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
Description
Verfahren zur Darstellung eines basischen Derivates einer substituierten Chinolinearbonsäure. Es wurde gefunden, da.ss man zu einem basischen Derivat einer substituierten Chino- lincarbonsäure gelangt,
wenn man .auf Särure- ha.logenide der 2-Halogen-4-ebinolincarbon- säure Triäthyläthylendiamin einwirken lässt und das erhalten & 2-@Halogen-4-ehinolincar- bonsäure-triKthyläthylendiamid mit Mitteln, die zur Einführung der Iso-a.myloxygruppe dienen, umsetzt.
Das 2-Iso-amyloxy-4--chinoli'ncarbon.säure- t.riäthyläthylendiamid bildet ein hellgelbes 01 vom Siedepunkt 165-168 bei 0,01 mm Druck. Die Base ist in organischen Lösungs mitteln leicht löslich. Mit Säuren gibt sie neutrale, in Wasser leicht lösliche Salze.
Die neue Verbindung soll zu therapeu tischen Zwecken Verwendung finden. Beispiel: ,Zu einer Lösung von 1,5 Teilen Triäthyl- äthylendiamin (farblose Base vom Siedepunkt 160-165 , dargestellt durch Reduktion des Kondensationsproduktes aus a s.
Diäthyläthy- lendi.amin und Acetaldehyd vom Siedepunkt 40' bei 7 mm Druck) in 4 Teilen 10 % iger Natronlaugel l.ässt man unter Rühren und Kühlen eine benzolische Lösung von 2,2 Teilen 2aChlor-4,chinolinearb-o@nsänrechloWicl allmählich zufliessen.
Nach beendeter Reak tion wird. mit Wasser gewaschen und das Lösungsmittel abdestilliert. Das 2-Chlor-,4 chinolinearbonsäure-tri'ä,thyläthylendiamidbil- det ein gelbliches 01 vom Siedepunkt<B>165'</B> bei etwa 0,015 mm Druck. In organischen Lösungsmitteln ist es leicht löslich. Mit Säuren gibt die Base neutrale, wasserlösliche Salze.
33 Teile 2-Chlor-4-chinolincarbonsäure- triäthyläthylendiamid werden mit einer Lö sung von 2,5 Teilen Natrium in Iso-amyl- alkohol gekocht. Hierauf wird der Iso-amyl- alkohol im Vakuum abdestilliert .der Rück stand in' Äther aufgenommen und mit Wasser gewaschen. Nach Entfernung des Lösungs- mittels verbleibt das 2-Iso-amyloxy-4-chino- lincarbonsäure-triäthyläthylendiamid als hell- ge1-bes 01. Die Base lässt sich im Vakuum destillieren.
Zur Einführung der Iso-amyloxygruppe können auch andere Metall-iso-amylate in or ganischen Lösungsmitteln oder zum Beispiel Alkalien in Gegenwart von Iso-amylalkohol Verwendung finden.
Process for the preparation of a basic derivative of a substituted quinolinearboxylic acid. It has been found that a basic derivative of a substituted quinoline carboxylic acid is obtained,
if one lets act on acidic ha.logenide of 2-halo-4-ebinolinecarboxylic acid triethylethylenediamine and obtain 2- @ halo-4-ehinolinecarbonsäure-triKthyläthylendiamid with agents that introduce the iso-a.myloxy group serve, implement.
The 2-iso-amyloxy-4-quinoli'ncarbon.äur- t.riäthyläthylendiamid forms a light yellow oil with a boiling point 165-168 at 0.01 mm pressure. The base is 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. Example: To a solution of 1.5 parts of triethylethylenediamine (colorless base with a boiling point of 160-165, represented by reduction of the condensation product from a s.
Diethylethylenediamine and acetaldehyde with a boiling point of 40 'at 7 mm pressure) in 4 parts of 10% sodium hydroxide gel, a benzene solution of 2.2 parts of 2aChlor-4, quinolinearb-o @ nsänrechloWicl is allowed to flow in gradually with stirring and cooling .
When the reaction is complete. washed with water and the solvent was distilled off. The 2-chloro-, 4-quinolinearboxylic acid-tri'ä, thyläthylendiamid forms a yellowish oil with a boiling point <B> 165 '</B> at about 0.015 mm pressure. It is easily soluble in organic solvents. With acids, the base gives neutral, water-soluble salts.
33 parts of 2-chloro-4-quinolinecarboxylic acid triethylethylenediamide are boiled with a solution of 2.5 parts of sodium in iso-amyl alcohol. The iso-amyl alcohol is then distilled off in vacuo. The residue is taken up in ether and washed with water. After the solvent has been removed, the 2-iso-amyloxy-4-quinoline-carboxylic acid triethylethylenediamide remains as a light-yellow oil. The base can be distilled in vacuo.
To introduce the iso-amyloxy group, other metal iso-amylates in organic solvents or, for example, alkalis in the presence of iso-amyl alcohol can also be used.
Claims (1)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH139437T | 1927-11-19 | ||
| CH137338T | 1931-12-21 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH139437A true CH139437A (en) | 1930-04-15 |
Family
ID=25712947
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH139437D CH139437A (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) | CH139437A (en) |
-
1927
- 1927-11-19 CH CH139437D patent/CH139437A/en unknown
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