AT89921B - Process for the preparation of an oxyphenylquinolinedicarboxylic acid and its derivatives. - Google Patents
Process for the preparation of an oxyphenylquinolinedicarboxylic acid and its derivatives.Info
- Publication number
- AT89921B AT89921B AT89921DA AT89921B AT 89921 B AT89921 B AT 89921B AT 89921D A AT89921D A AT 89921DA AT 89921 B AT89921 B AT 89921B
- Authority
- AT
- Austria
- Prior art keywords
- acid
- derivatives
- oxyphenylquinolinedicarboxylic
- preparation
- parts
- Prior art date
Links
- 239000002253 acid Substances 0.000 title claims description 10
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 claims description 6
- LCTONWCANYUPML-UHFFFAOYSA-N Pyruvic acid Chemical compound CC(=O)C(O)=O LCTONWCANYUPML-UHFFFAOYSA-N 0.000 claims description 4
- MQMWPBBDMIYYMI-UHFFFAOYSA-N 2-aminophenylglyoxylic acid Chemical compound NC1=CC=CC=C1C(=O)C(O)=O MQMWPBBDMIYYMI-UHFFFAOYSA-N 0.000 claims description 3
- 229940107700 pyruvic acid Drugs 0.000 claims description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 4
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 4
- 150000001875 compounds Chemical class 0.000 description 4
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- 239000000243 solution Substances 0.000 description 3
- JXDYKVIHCLTXOP-UHFFFAOYSA-N isatin Chemical compound C1=CC=C2C(=O)C(=O)NC2=C1 JXDYKVIHCLTXOP-UHFFFAOYSA-N 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 1
- QXNVGIXVLWOKEQ-UHFFFAOYSA-N Disodium Chemical class [Na][Na] QXNVGIXVLWOKEQ-UHFFFAOYSA-N 0.000 description 1
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 1
- 208000025747 Rheumatic disease Diseases 0.000 description 1
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 1
- 239000012670 alkaline solution Substances 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 238000002425 crystallisation Methods 0.000 description 1
- 230000008025 crystallization Effects 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 230000020477 pH reduction Effects 0.000 description 1
- -1 phenylquinoline oxydicarboxylic acid Chemical compound 0.000 description 1
Landscapes
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Description
<Desc/Clms Page number 1>
EMI1.1
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mit Isatinsäure eine für medizinische Zwecke, zur Behandlung von gichtisch-rheumatischen Erkrankungen, wertvolle Verbindung, nämlich eine Oxyphenylchinolindikarbonsäure, gewonnen wird. Die I'msetzung jener Verbindungen vollzieht sich im Sinne der folgenden Formelgleichung :
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Die neue Verbindung ist unlöslich in Wasser und Ligroin, schwer löslich in Alkohol und Methylalkohol.
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Auch kann man Derivate der Oxyphenylchinolindikarbonsäure herstellen, welche dieser letzteren sehr ähnlich sind. indem man an Stelle von Anilin dessen Homologe oder Derivate oder an Stelle von Azetosalizylsäure deren Homologe. wie Azeto-o-kresotinsäure oder Azeto-m-kresotinsäure oder auch an Stelle von Isatinsäure deren Derivate, wie beispielsweise Methylendioxyi atinsäure, verwendet.
Beispiel 1 : Zu der durch Auflösung von 147 Teilen Isatin in 600 Teilen 33% iger Kalilauge
EMI1.5
etwa acht Stunden auf dem Wasserbad erwärmt. Aus der Lösung wird sodann die Oxyphenylchinolindikarbonsäure durch Salzsäure gefällt, abfiltriert und mit warmem Alkohol ausgewaschen. Gegebenenfalls kann sie. durch Kristallisation ihres Dinatriumsalzes oder ihres Diäthylesters vom Schmelzpunkt 103 , welche in bekannter Weise erhältlich sind, gereinigt werden.
Beispiel 2 : lss6 Teile p-Aldehydosalizylsäure werden mit 93 Teilen Anilin in 1000 Teilen Alkohol gelöst. Zu der Lösung der entstehenden Verbindung werden 88 Teile Brenztraubensäure zugegeben und 3 his 4 Stunden zum Sieden erhitzt. Nach dem Abdestillieren des Alkohols wird der Rückstand mit Sodalösung aufgenommen und aus der alkalischen Lösung die Phenylchinolinoxydikarbonsäure durch Ansäuern mit Salzsäure gefällt. Um sie chemisch rein zu erhalten, kann man verfahren, wie im Beispiel 1 angegeben ist.
**WARNUNG** Ende DESC Feld kannt Anfang CLMS uberlappen**.
<Desc / Clms Page number 1>
EMI1.1
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with isatic acid a compound valuable for medical purposes, for the treatment of gouty-rheumatic diseases, namely an oxyphenylquinolinedicarboxylic acid, is obtained. The implementation of these compounds takes place in the sense of the following formula:
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The new compound is insoluble in water and ligroin, sparingly soluble in alcohol and methyl alcohol.
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It is also possible to prepare derivatives of oxyphenylquinolinedicarboxylic acid, which are very similar to the latter. by using its homologues or derivatives in place of aniline or their homologues in place of acetosalicylic acid. such as azeto-o-cresotinic acid or azeto-m-cresotinic acid or, instead of isatic acid, their derivatives, such as methylenedioxyi atinic acid, are used.
Example 1: To that obtained by dissolving 147 parts of isatin in 600 parts of 33% potassium hydroxide solution
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warmed on the water bath for about eight hours. The oxyphenylquinolinedicarboxylic acid is then precipitated from the solution with hydrochloric acid, filtered off and washed out with warm alcohol. If necessary, it can. by crystallization of their disodium salt or their diethyl ester of melting point 103, which can be obtained in a known manner.
Example 2: 6 parts of p-aldehydosalicylic acid are dissolved with 93 parts of aniline in 1000 parts of alcohol. 88 parts of pyruvic acid are added to the solution of the compound formed and the mixture is heated to boiling for 3 to 4 hours. After the alcohol has been distilled off, the residue is taken up with soda solution and the phenylquinoline oxydicarboxylic acid is precipitated from the alkaline solution by acidification with hydrochloric acid. In order to get them chemically pure, one can proceed as indicated in Example 1.
** WARNING ** End of DESC field may overlap beginning of CLMS **.
Claims (1)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| AT89921T | 1914-12-01 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| AT89921B true AT89921B (en) | 1922-11-10 |
Family
ID=3610255
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| AT89921D AT89921B (en) | 1914-12-01 | 1914-12-01 | Process for the preparation of an oxyphenylquinolinedicarboxylic acid and its derivatives. |
Country Status (1)
| Country | Link |
|---|---|
| AT (1) | AT89921B (en) |
-
1914
- 1914-12-01 AT AT89921D patent/AT89921B/en active
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