AT69846B - Process for the preparation of quinoline-4-carboxylic acids arylated in the 2-position. - Google Patents
Process for the preparation of quinoline-4-carboxylic acids arylated in the 2-position.Info
- Publication number
- AT69846B AT69846B AT69846DA AT69846B AT 69846 B AT69846 B AT 69846B AT 69846D A AT69846D A AT 69846DA AT 69846 B AT69846 B AT 69846B
- Authority
- AT
- Austria
- Prior art keywords
- arylated
- quinoline
- preparation
- carboxylic acids
- alcohol
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims description 3
- VQMSRUREDGBWKT-UHFFFAOYSA-N quinoline-4-carboxylic acid Chemical class C1=CC=C2C(C(=O)O)=CC=NC2=C1 VQMSRUREDGBWKT-UHFFFAOYSA-N 0.000 title description 2
- 230000001476 alcoholic effect Effects 0.000 claims 1
- 230000005494 condensation Effects 0.000 claims 1
- 238000009833 condensation Methods 0.000 claims 1
- LCTONWCANYUPML-UHFFFAOYSA-N Pyruvic acid Chemical compound CC(=O)C(O)=O LCTONWCANYUPML-UHFFFAOYSA-N 0.000 description 8
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 6
- 229940107700 pyruvic acid Drugs 0.000 description 4
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- SATCULPHIDQDRE-UHFFFAOYSA-N piperonal Chemical compound O=CC1=CC=C2OCOC2=C1 SATCULPHIDQDRE-UHFFFAOYSA-N 0.000 description 2
- BXJGDSAEIGHCPT-UHFFFAOYSA-N 2-(1,3-benzodioxol-5-ylmethyl)-8-methoxyquinoline-4-carboxylic acid Chemical compound COC=1C=CC=C2C(=CC(=NC12)CC1=CC=2OCOC2C=C1)C(=O)O BXJGDSAEIGHCPT-UHFFFAOYSA-N 0.000 description 1
- IKVSQHOTFICZGX-UHFFFAOYSA-N 2-(1,3-benzodioxol-5-ylmethyl)quinoline-4-carboxylic acid Chemical compound C1=CC=C2C(C(=O)O)=CC(CC=3C=C4OCOC4=CC=3)=NC2=C1 IKVSQHOTFICZGX-UHFFFAOYSA-N 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- VMPITZXILSNTON-UHFFFAOYSA-N o-anisidine Chemical compound COC1=CC=CC=C1N VMPITZXILSNTON-UHFFFAOYSA-N 0.000 description 1
- 229940081310 piperonal Drugs 0.000 description 1
Landscapes
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Description
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Alkohol in der vorbeschriebenen Weise gegeben. Die Ausbeute an roher 2-Piperonylchinolin- -4-karbonsäure beträgt etwa 205% der ungewandten Brenztraubcnsäuro.
Beispiel 5 : 123 Teile o-Anisidin, 1, 50 Teile Piperonal werden in 750 Teilen absolutem Alkohol wie oben gekocht und dann mit 66 Teilen Brenztraubensäure in 150'l eilen Alkohol in der angegebenen Weise weiterbehandelt. Die Ausbeute beträgt etwa 205% der angewandten Brenztraubensäure.
Die bisher unbekannte 2-Piperonyl-8-methoxychinolin-4-karbonsäure bildet, aus 50% igem Alkohol umkristallisiert, rotbraune Kristalle, die bei 105 bis 1100 getrocknet, zwisehen 162 bis 170 allmählich schmelzen. Die Verbindung ist geschmarkfrei und löslich in Alkohol, schwerer löslich in Äther.
PATENT-ANSPRÜCHE :
1. Abänderung des durch Patent Nr. 63525 und dessen Zusatzpatent Nr. 68501 geschützten Verfahrens zur Darstellung von in 2-Stellung arylierten Chinolin-4-karbonsäuren, dadurch gekennzeichnet, das man weniger als 1 Molekül Brenztraubensäure anwendet.
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Alcohol given in the manner described above. The yield of crude 2-piperonylquinoline-4-carboxylic acid is about 205% of the unused pyruvic acid.
Example 5 123 parts of o-anisidine, 1.5 parts of piperonal are boiled in 750 parts of absolute alcohol as above and then treated further in the manner indicated with 66 parts of pyruvic acid in 150 liters of alcohol. The yield is about 205% of the pyruvic acid used.
The hitherto unknown 2-piperonyl-8-methoxyquinoline-4-carboxylic acid, recrystallized from 50% alcohol, forms red-brown crystals which, when dried at 105 to 1100, gradually melt between 162 to 170. The compound is free of smear and soluble in alcohol, less soluble in ether.
PATENT CLAIMS:
1. Modification of the process protected by patent no. 63525 and its additional patent no. 68501 for the preparation of quinoline-4-carboxylic acids arylated in the 2-position, characterized in that less than 1 molecule of pyruvic acid is used.
Claims (1)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE63525X | 1911-07-05 | ||
| DE69846X | 1913-08-01 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| AT69846B true AT69846B (en) | 1915-09-10 |
Family
ID=25749382
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| AT69846D AT69846B (en) | 1911-07-05 | 1914-04-23 | Process for the preparation of quinoline-4-carboxylic acids arylated in the 2-position. |
Country Status (1)
| Country | Link |
|---|---|
| AT (1) | AT69846B (en) |
-
1914
- 1914-04-23 AT AT69846D patent/AT69846B/en active
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