DE626355C - Process for the preparation of esters of 2-phenylquinoline-4-carboxylic acid or their substitution products and homologues - Google Patents
Process for the preparation of esters of 2-phenylquinoline-4-carboxylic acid or their substitution products and homologuesInfo
- Publication number
- DE626355C DE626355C DEJ48330D DEJ0048330D DE626355C DE 626355 C DE626355 C DE 626355C DE J48330 D DEJ48330 D DE J48330D DE J0048330 D DEJ0048330 D DE J0048330D DE 626355 C DE626355 C DE 626355C
- Authority
- DE
- Germany
- Prior art keywords
- carboxylic acid
- phenylquinoline
- esters
- homologues
- preparation
- 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.)
- Expired
Links
Description
Verfahren zur Darstellung von Estern der 2-Phenylchinolin-4-carbonsäure oder ihrer Substitutionsprodukte und Homologen Es wurde gefunden, daß man durch Veresterung der 2-Phenylchinolin-4-carbonsäure, ihrer Substitutionsprodukte oder Homologen mit Glycerin oder durch Einwirkung von Halogenhydrinen desselben auf.diese Säuren zu bisher nicht beschriebenen Verbindungen gelangen kann, welche sowohl therapeutische Anwendung finden können als auch Zwischenprodukte bei Erlangung anderer gleichfalls praktisch brauchbarer Stoffe darstellen. Weiter wurde festgestellt, daß sich die so gewonnenen halogenhaltigen Verbindungen auch mit den Alkalisalzen der Säuren umsetzen lassen. ' Beispiel i 5 Gewichtsteile 2-Phenylchinolin-4-carbonsäure, 7o Gewichtsteile Glycerin und 16,6 Gewichtsteile Schwefelsäure (D. 1,84) werden einige Stunden auf dem Wasserbade erwärmt. Dann wird alkalisch gemacht, der Niederschlag gewaschen, getrocknet und das Produkt durch Überführung in das Hydrochlorid gereinigt. Aus Benzol kristallisieren weiße 'adeln aus, die bei 99° schmelzen und in den gebräuchlichen Alkoholen, Äther und Benzol löslich sind.Process for the preparation of esters of 2-phenylquinoline-4-carboxylic acid or their substitution products and homologues. It has been found that by Esterification of 2-phenylquinoline-4-carboxylic acid, its substitution products or Homologues with glycerol or due to the action of halohydrins on these Acids can reach compounds not previously described, which are both therapeutic Can be used as well as intermediates when obtaining other products as well represent practically useful substances. It was also found that the Halogen-containing compounds obtained in this way also with the alkali salts of acids have it implemented. 'Example i 5 parts by weight of 2-phenylquinoline-4-carboxylic acid, 7o Parts by weight of glycerine and 16.6 parts by weight of sulfuric acid (D. 1.84) are some Heated for hours on the water bath. Then it is made alkaline, the precipitate washed, dried and the product purified by converting it into the hydrochloride. White 'needles' crystallize out of benzene, which melt at 99 ° and in the usual Alcohols, ethers and benzene are soluble.
Bei Behandlung von 2-Phenylchinolin-4-carbonsäurechlorid mit Glycerin oder Erwärmen von 2-phenylchinolin-4-carbonsaurem Kalium mit Glycerin-a-chlorhydrin entsteht gleichfalls der 2-Pheny lchinolin-4-carborlsäureglycerinester.When treating 2-phenylquinoline-4-carboxylic acid chloride with glycerine or heating of 2-phenylquinoline-4-carboxylic acid potassium with glycerol-α-chlorohydrin The 2-phenylquinoline-4-carboric acid glycerol ester is also formed.
Der analog gewonnene Ester der 2-Phenyl-6-methoxvchinoIin-4-carbonsäure schmilzt bei 167°, der 2-(p-Tolyl)-chinolin-4-carbonsäureglycerinester bei i io,5°, der 2-Phenylchü, nolzn-4'-carbonsäureglycerinester kommt aus Benzol in farblosen Platten vom F. z13°.The ester of 2-phenyl-6-methoxyquinoline-4-carboxylic acid obtained analogously melts at 167 °, the 2- (p-tolyl) -quinoline-4-carboxylic acid glycerol ester at 10.5 °, the 2-phenylchü, nolzn-4'-carboxylic acid glycerol ester comes from benzene in colorless form Plates from the F. z13 °.
Beispiel e 3o Gewichtsteile 2-phenylchinohn-4-carbonsaures Kalium und 6,7 Gewichtsteile Glycerins, a-dichlorhydrin werden io bis 2o Stunden auf 16o bis 17o° erhitzt. Dann wird mit Natriumcarbonat verrieben, gewaschen, .nit Äther extrahiert und im Vakuum getrocknet. Zwecks weiterer Reinigung wird in Olivenöl gelöst und mit Petroläther gefällt. Der so erhaltene a, a'-Bis- (2-phenylchinolin-4-carbonsäure)-glycerinester stellt dann ein in den üblichen Alkoholen leicht lösliches weißes Pulver dar, das bei 58° schmilzt.Example e 3o parts by weight of 2-phenylquinone-4-carboxylic acid potassium and 6.7 parts by weight of glycerol, a-dichlorohydrin are 10 to 20 hours to 16o heated to 17o °. Then it is triturated with sodium carbonate, washed, with ether extracted and dried in vacuo. For further cleaning it is in olive oil dissolved and precipitated with petroleum ether. The a, a'-bis (2-phenylquinoline-4-carboxylic acid) glycerol ester thus obtained then represents a white powder that is easily soluble in common alcohols melts at 58 °.
Zu empirisch gleich zusammengesetzten Verbindungen gelangt man durch Einwirkung von dem im Beispiel 4 genannten 2-Phenylchinolin -4- carbonsäure-(y-chlorpr opandiol)-a-ester auf das erwähnte Kaliumsalz oder durch Erhitzen von 2 Mol des Säurechlorides mit i Mol Glycerin.You get through to compounds that are empirically composed in the same way Action of the 2-phenylquinoline -4-carboxylic acid (y-chloropr opandiol) -a-ester on the mentioned potassium salt or by heating 2 mol of the Acid chlorides with 1 mole of glycerine.
Der analog bereitete a, a'-Bis-(2-phenyl-6 - methoxychinolin - 4- carbonsäure)-glycerinester schmilzt bei 92 bis 94°, der a, ä -Bis-(2 -p - tolylchinolin -.4- carbonsäure)- glycerinester bei 73 bis 75°, der a, ß-Bis-(2-phenvlchinolin-4-carbonsäure)-glycerinester bei 65 bis 68°.The a, a'-bis- (2-phenyl-6-methoxyquinoline-4-carboxylic acid) -glycerol ester, prepared analogously, melts at 92 to 94 °, the a, a- bis- (2-p-tolylquinoline-4-carboxylic acid ) - glycerol ester at 73 to 75 °, the α, ß-bis (2-phenylquinoline-4-carboxylic acid) glycerol ester at 65 to 68 °.
Beispiel 3 3,6Gewichtsteile2-Phenylchinolin-4-carbonsäure-ß, ß'-dichlorisopropylester und 5,8 Gewichtsteile 2-phenylchinolin-4-carbonsaures Kalium werden to bis 2o Stunden auf 16o bis. 17o° erhitzt. Dann wird mit Natriumcarbonat verrieben, gewaschen, mit Äther extrahiert- und im Vakuum getrocknet. Zwecks Reinigung wird aus Amylalkohol und aus Benzol umkristallisiert. Der so erhaltene a, ß', y-Tri-(2-phenylchinolin-q.-carbonsäure)-glycerinester schmilzt bei z35°.Example 3 3.6 parts by weight of 2-phenylquinoline-4-carboxylic acid ß, ß'-dichloroisopropyl ester and 5.8 parts by weight of 2-phenylquinoline-4-carboxylic acid Be potassium to up to 2o hours to 16o to. Heated to 17o °. Then it is triturated with sodium carbonate, washed, extracted with ether and dried in vacuo. Purpose of cleaning is recrystallized from amyl alcohol and from benzene. The α, β ', γ-tri- (2-phenylquinoline-q.-carboxylic acid) glycerol ester obtained in this way melts at z35 °.
Beispiel 4 9,5 Gewichtsteilez-Phenylchinolin-4-carbonsäurechlorid und 3,5 Gewichtsteile Glycerina-chlorhydrin (in etwa 7o Gewichtsteilen Benzol) werden bis zur Beendigung der Salzsäureentwicklung auf dem Wasserbade erhitzt; dann wird das Lösungsmittel abdestilliert, der Rückstand mit N atriumcarbonat verrieben, gewaschen, in Äther gelöst und nach Filtration der Äther entfernt. Aus Alkohol kristallisiert der g-Phenylchinolin - 4 - carbonsäure - y - chlorpröpaiidiola-ester in farblosen Nadeln vom E. iog°-Die Verwendung von Glycerin-*,_ a-dichlorhydrin führt zum 2-Phenylclzinolin-4-carbonsäure-ß, ß'-dichlorisopropylester, der sich aus Alkohol in farblosen, monoklinen Kristallen ausscheidet, die bei g6° schmelzen. Die Einwirkung von i Mol Glycerin-a-chlorhydrin auf 2 Mol des Säurechlorides ergibt den a, ß-Bis-(2-phenylchinolin-4-carbonsäure)-y-chlorpropandiolester vom F. i35°. Der 2-(p-Tolylchinolin-4-carbonsäure)-ß, ß'-dichlorisf)propylester schmilzt bei ioi°.EXAMPLE 4 9.5 parts by weight of z-phenylquinoline-4-carboxylic acid chloride and 3.5 parts by weight of glycerine chlorohydrin (in about 70 parts by weight of benzene) are heated on the water bath until the evolution of hydrochloric acid has ceased; then the solvent is distilled off, the residue is triturated with sodium carbonate, washed, dissolved in ether and, after filtration, the ether is removed. The g-phenylquinoline-4-carboxylic acid-y-chlorpröpaiidiola-ester crystallizes from alcohol in colorless needles from E. iog ° -The use of glycerine - *, _ a-dichlorohydrin leads to 2-phenylclzinoline-4-carboxylic acid-ß, ß '-dichloroisopropyl ester, which is precipitated from alcohol in colorless, monoclinic crystals which melt at g6 °. The action of 1 mole of glycerol-a-chlorohydrin on 2 moles of the acid chloride gives the α, β-bis (2-phenylquinoline-4-carboxylic acid) -y-chloropropanediol ester with a temperature of 135 °. The 2- (p-tolylquinoline-4-carboxylic acid) -ß, ß'-dichloroisf) propyl ester melts at ioi °.
Claims (1)
Priority Applications (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
DEJ48330D DE626355C (en) | 1933-11-12 | 1933-11-12 | Process for the preparation of esters of 2-phenylquinoline-4-carboxylic acid or their substitution products and homologues |
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
DEJ48330D DE626355C (en) | 1933-11-12 | 1933-11-12 | Process for the preparation of esters of 2-phenylquinoline-4-carboxylic acid or their substitution products and homologues |
Publications (1)
Publication Number | Publication Date |
---|---|
DE626355C true DE626355C (en) | 1936-02-25 |
Family
ID=7206559
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
DEJ48330D Expired DE626355C (en) | 1933-11-12 | 1933-11-12 | Process for the preparation of esters of 2-phenylquinoline-4-carboxylic acid or their substitution products and homologues |
Country Status (1)
Country | Link |
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DE (1) | DE626355C (en) |
Cited By (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
DE1106764B (en) * | 1957-09-20 | 1961-05-18 | Hefa G M B H Chemisch Pharmaze | Process for the preparation of bis (2-phenyl-quinoline- (4) -carboxylic acid) -glycerol esters suitable as agents against colds |
-
1933
- 1933-11-12 DE DEJ48330D patent/DE626355C/en not_active Expired
Cited By (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
DE1106764B (en) * | 1957-09-20 | 1961-05-18 | Hefa G M B H Chemisch Pharmaze | Process for the preparation of bis (2-phenyl-quinoline- (4) -carboxylic acid) -glycerol esters suitable as agents against colds |
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