CH139431A - 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
- CH139431A CH139431A CH139431DA CH139431A CH 139431 A CH139431 A CH 139431A CH 139431D A CH139431D A CH 139431DA CH 139431 A CH139431 A CH 139431A
- Authority
- CH
- Switzerland
- Prior art keywords
- acid
- preparation
- carboxylic acid
- petroleum ether
- basic derivative
- Prior art date
Links
- LOAUVZALPPNFOQ-UHFFFAOYSA-N quinaldic acid Chemical class C1=CC=CC2=NC(C(=O)O)=CC=C21 LOAUVZALPPNFOQ-UHFFFAOYSA-N 0.000 title claims description 5
- 238000000034 method Methods 0.000 title claims description 3
- 238000002360 preparation method Methods 0.000 title claims description 3
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 14
- 239000002253 acid Substances 0.000 claims description 9
- 239000003208 petroleum Substances 0.000 claims description 6
- 239000013078 crystal Substances 0.000 claims description 4
- 239000003960 organic solvent Substances 0.000 claims description 4
- 150000007513 acids Chemical class 0.000 claims description 3
- 125000002933 cyclohexyloxy group Chemical group C1(CCCCC1)O* 0.000 claims description 3
- 238000002844 melting Methods 0.000 claims description 3
- 230000008018 melting Effects 0.000 claims description 3
- 230000007935 neutral effect Effects 0.000 claims description 3
- 150000003839 salts Chemical class 0.000 claims description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 3
- 239000003795 chemical substances by application Substances 0.000 claims description 2
- 230000001225 therapeutic effect Effects 0.000 claims description 2
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 6
- CJKRXEBLWJVYJD-UHFFFAOYSA-N N,N'-diethylethylenediamine Chemical compound CCNCCNCC CJKRXEBLWJVYJD-UHFFFAOYSA-N 0.000 description 5
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- RONMETJMOIJEGF-UHFFFAOYSA-N 2-cyclohexyloxyquinoline-4-carboxylic acid Chemical compound N=1C2=CC=CC=C2C(C(=O)O)=CC=1OC1CCCCC1 RONMETJMOIJEGF-UHFFFAOYSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- 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
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- HPXRVTGHNJAIIH-UHFFFAOYSA-N cyclohexanol Chemical compound OC1CCCCC1 HPXRVTGHNJAIIH-UHFFFAOYSA-N 0.000 description 1
- 150000004820 halides Chemical class 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 239000000203 mixture 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)
- Quinoline Compounds (AREA)
Description
Verfahren zur Darstellung eines basischen Derivates einer substituierten Chinolincarbonsäure. Es wurde gefunden, dass man zu einem basischen Derivat einer substituierten Chino-lincarbonsäure gelang-, wenn man auf Säurehalogenide der 2-Halogen-4-chinolincar- bonsäure asymmetrisches Diäthyläthyiendia- min einwirken lässt und das erhaltene 2 Halogen-4-,
chinolincarbonsäure - diäthylä@thy- lendiamid mit alkalischen Mitteln, die zur Einführung der Cyclohexyloxygruppe dienen, umsetzt.
Das 2-Cyclohexyloxy-4-chinolincarbon- säure-diäthyläthylendiami$ bildet farblose Kristalle vom ,Schmelzpunkt 69 . Die Base ist in kaltem Petroläther schwer löslich; in war mem Petroläther, wie in den übrigen orga nischen Lösungsmitteln ist sie leicht löslich. Mit Säuren gibt sie neutrale, in Wasser leicht lösliche Salze.
Die neue Verbindung soll zu therapeuti schen Zwecken Verwendung finden. <I>Beispiel:</I> Zu einer Lösung von 1,2 Teilen asymme trischem Diäthyläthylendiamin in 45 Teilen 10% iger Natronlauge gibt man unter Küh lung und .gändigem Umrühren allmählich eine benzolische Lösung von 2,2 Teilen 2- Chlor-4-cIiinolincarbonsäureGhlo,rid zu. Nach beendigter Reaktion wird die benzolische Lö sung abgetrennt, ..die gebildete Base mit Salz säure ausgezogen und mit Soda wieder aus gefällt.
Man nimmt die Base in Äther auf, vertreibt das Lösungsmittel und kristallisiert aus Petroläther um. Dass 2-Chlor-4-chinolin- carbonsäure-,diäthyläthylendiamidbildet farb lose, blättrige Kristalle vom Schmelzpunkt 74'.
In den meisten organischen Lösungs- mitteln ist die Base leicht löslich; mit Säu ren bildet sie neutrale, was.serlösliche Salze.
2;6 Teile Natrium werden mit 12 Teilen Cyelo@hexylalkoh.ol durch Erwärmen in To luollösung umgesetzt. Hierauf gibt man 30 Teile 2-Chlor-4-cIiinolincarbo@nsäure-diäthyl- äthylendiamid hinzu und erwärmt im 01bad bis zur Beendigung der Reaktion. Man wäscht mit Wasser aus und destilliert das Lösungsmittel im Vakuum ab. Man erhält das 2-Cyclohexyloxy-4-chinolincarbonsäure- diäthylätliylendiamid als 01, das alsbald zu farblosen Kristallen erstarrt.
Die Baue lässt sich aus Petroläther umkristallisieren.
Zur Einführung der Cyclohexyloxygruppe können .auch andere Metallcyklohexylate in organischen Lösungsmitteln oder zum Bei spiel auch Alkalien in Gegenwart von Cyelo- liexylalkohol Verwendung finden.
Process for the preparation of a basic derivative of a substituted quinoline carboxylic acid. It has been found that a basic derivative of a substituted quinolinecarboxylic acid is obtained if asymmetric diethylethylenediamine is allowed to act on acid halides of 2-halo-4-quinolinecarboxylic acid and the 2 halo-4-,
quinoline carboxylic acid - diethylä @ thy- lendiamid with alkaline agents that are used to introduce the cyclohexyloxy group.
The 2-cyclohexyloxy-4-quinolinecarboxylic acid diethyläthylendiami $ forms colorless crystals with a melting point of 69. The base is sparingly soluble in cold petroleum ether; In war mem petroleum ether, as in the other organic solvents, it is easily soluble. 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 1.2 parts of asymmetric diethylethylenediamine in 45 parts of 10% sodium hydroxide solution, a benzene solution of 2.2 parts of 2-chloro-4 is gradually added with cooling and stirring -cIiinolinecarbonsäureGhlo, rid to. After the reaction has ended, the benzene solution is separated off, .. the base formed is extracted with hydrochloric acid and precipitated again with soda.
The base is taken up in ether, the solvent is driven off and recrystallized from petroleum ether. That 2-chloro-4-quinolinecarboxylic acid, diethylethylenediamide forms colorless, leafy crystals with a melting point of 74 '.
The base is easily soluble in most organic solvents; with acids it forms neutral, soluble salts.
2; 6 parts of sodium are reacted with 12 parts of Cyelo@hexylalkoh.ol by heating in a toluene solution. Then 30 parts of 2-chloro-4-quinolinecarbonic acid diethyl ethylenediamide are added and the mixture is heated in the oil bath until the reaction is complete. It is washed with water and the solvent is distilled off in vacuo. The 2-cyclohexyloxy-4-quinolinecarboxylic acid diethylethylenediamide is obtained as 01, which soon solidifies to form colorless crystals.
The structure can be recrystallized from petroleum ether.
Other metal cyclohexylates in organic solvents or, for example, alkalis in the presence of cyclohexyl alcohol can also be used to introduce the cyclohexyloxy group.
Claims (1)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH139431T | 1927-11-19 | ||
| CH137338T | 1931-12-21 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH139431A true CH139431A (en) | 1930-04-15 |
Family
ID=25712941
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH139431D CH139431A (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) | CH139431A (en) |
-
1927
- 1927-11-19 CH CH139431D patent/CH139431A/en unknown
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