DE244788C - - Google Patents
Info
- Publication number
- DE244788C DE244788C DENDAT244788D DE244788DA DE244788C DE 244788 C DE244788 C DE 244788C DE NDAT244788 D DENDAT244788 D DE NDAT244788D DE 244788D A DE244788D A DE 244788DA DE 244788 C DE244788 C DE 244788C
- Authority
- DE
- Germany
- Prior art keywords
- phenylquinoline
- carboxylic acid
- esters
- water
- alcohol
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Active
Links
- YTRMTPPVNRALON-UHFFFAOYSA-N Cinchophen Chemical compound N=1C2=CC=CC=C2C(C(=O)O)=CC=1C1=CC=CC=C1 YTRMTPPVNRALON-UHFFFAOYSA-N 0.000 claims description 5
- 150000007860 aryl ester derivatives Chemical class 0.000 claims description 3
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Natural products OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 claims description 2
- 238000002360 preparation method Methods 0.000 claims description 2
- UFWIBTONFRDIAS-UHFFFAOYSA-N Naphthalene Natural products C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 claims 1
- 150000002790 naphthalenes Chemical class 0.000 claims 1
- 150000002989 phenols Chemical class 0.000 claims 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 5
- XHXFXVLFKHQFAL-UHFFFAOYSA-N Phosphoryl chloride Chemical compound ClP(Cl)(Cl)=O XHXFXVLFKHQFAL-UHFFFAOYSA-N 0.000 description 4
- RTZKZFJDLAIYFH-UHFFFAOYSA-N diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 4
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 2
- 150000002148 esters Chemical class 0.000 description 2
- 238000002844 melting Methods 0.000 description 2
- JWAZRIHNYRIHIV-UHFFFAOYSA-N 2-Naphthol Chemical compound C1=CC=CC2=CC(O)=CC=C21 JWAZRIHNYRIHIV-UHFFFAOYSA-N 0.000 description 1
- 206010039073 Rheumatoid arthritis Diseases 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- 235000019658 bitter taste Nutrition 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 125000004494 ethyl ester group Chemical group 0.000 description 1
- 201000005569 gout Diseases 0.000 description 1
- 125000004492 methyl ester group Chemical group 0.000 description 1
- -1 phenyl ester Chemical class 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 230000001225 therapeutic Effects 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
- C07D215/52—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen attached in position 4 with aryl radicals attached in position 2
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
Description
KAISERLICHESIMPERIAL
PATENTAMT.PATENT OFFICE.
PATENTSCHRIFTPATENT LETTERING
- JVl 244788'-KLASSE Λ2ρ. GRUPPE!.- JVl 244788'-CLASS Λ2ρ. GROUP!.
Patentiert im Deutschen Reiche vom 1. März 1911 ab.Patented in the German Empire on March 1, 1911.
Von den Estern der 2-Phenylchinolin-4-carbonsäure, die als Mittel gegen Gicht und Gelenkrheumatismus Verwendung findet, sind bisher nur der Methyl- und Äthylester bekannt (vgl. Ann. 282 [1894], S. 106, und Journ. f. pr. Chem. N. F. 56 [1897], S. 297), die aber wegen ihres bitteren Geschmackes für therapeutische Zwecke nicht besonders geeignet sind. Die Arylester dagegen sind, wie gefunden wurde, völlig geschmacklos. Sie werden nach den für die Darstellung von Estern üblichen Methoden gewonnen.From the esters of 2-phenylquinoline-4-carboxylic acid, which are used as a remedy for gout and rheumatoid arthritis Is used, only the methyl and ethyl esters are known so far (cf. Ann. 282 [1894], p. 106, and Journ. f. pr. Chem. N.F. 56 [1897], p. 297), but because of their bitter taste are not particularly suitable for therapeutic purposes. the In contrast, aryl esters have been found to be completely tasteless. You will be after the obtained for the preparation of esters usual methods.
i. 100 g 2-Phenylchinolin-4-carbonsäure werden mit 75 g Phenol auf i8o° erhitzt und unter Rühren und Schütteln mit V2 Molekül Phosphoroxychlorid versetzt. Nach Beendigung der Reaktion wird die Masse in kaltes Wasser gegossen und aus Alkohol umkristallisiert. Der Phenylester ist in Wasser unlöslich, in Alkohol und Äther löslich. Er hat einen Schmelzpunkt von 132 °.i. 100 g of 2-phenylquinoline-4-carboxylic acid are heated to 180 ° with 75 g of phenol and V 2 molecules of phosphorus oxychloride are added while stirring and shaking. After the reaction has ended, the mass is poured into cold water and recrystallized from alcohol. The phenyl ester is insoluble in water, soluble in alcohol and ether. It has a melting point of 132 °.
In analoger Weise gelangt man zu anderen Arylestern.Other aryl esters are obtained in an analogous manner.
2. 25 g 2-Phenylchinolin-4-carbonsäure werden mit 14,5 g ß-Naphtol in etwa 150 ecm trocknem Benzol erwärmt und dazu allmählich 7,7 g Phosphoroxychlorid gegeben. Nach Y2- bis V4stündigem Kochen auf dem Wasserbade wird die Lösung in viel heißes Wasser gegossen und das ausgefallene Reaktionsprodukt durch Umkristallisieren gereinigt. Die Verbindung ist löslich in Äther und heißem Alkohol, unlöslich in Wasser und Alkali. Die gelblich gefärbten Kristalle haben einen Schmelzpunkt von 130 °.2. 25 g of 2-phenylquinoline-4-carboxylic acid are heated with 14.5 g of β-naphthol in about 150 ecm of dry benzene and 7.7 g of phosphorus oxychloride are gradually added. After Y 2 to V 4 hours of boiling on the water bath, the solution is poured into plenty of hot water and the precipitated reaction product is purified by recrystallization. The compound is soluble in ether and hot alcohol, insoluble in water and alkali. The yellowish colored crystals have a melting point of 130 °.
Claims (1)
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE244788C true DE244788C (en) |
Family
ID=503795
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DENDAT244788D Active DE244788C (en) |
Country Status (1)
| Country | Link |
|---|---|
| DE (1) | DE244788C (en) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0384313A1 (en) * | 1989-02-22 | 1990-08-29 | BASF Aktiengesellschaft | Quinoline-4-carboxylic acid derivatives and their application |
-
0
- DE DENDAT244788D patent/DE244788C/de active Active
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0384313A1 (en) * | 1989-02-22 | 1990-08-29 | BASF Aktiengesellschaft | Quinoline-4-carboxylic acid derivatives and their application |
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