CH182958A - Process for the preparation of a new ester of 2-phenylquinoline-4-carboxylic acid. - Google Patents

Process for the preparation of a new ester of 2-phenylquinoline-4-carboxylic acid.

Info

Publication number
CH182958A
CH182958A CH182958DA CH182958A CH 182958 A CH182958 A CH 182958A CH 182958D A CH182958D A CH 182958DA CH 182958 A CH182958 A CH 182958A
Authority
CH
Switzerland
Prior art keywords
carboxylic acid
phenylquinoline
preparation
new ester
dichlorohydrin
Prior art date
Application number
Other languages
German (de)
Inventor
John Hanns Univ Dr Prof
Original Assignee
John Hanns Univ Dr Prof
Priority date (The priority date 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 date listed.)
Filing date
Publication date
Application filed by John Hanns Univ Dr Prof filed Critical John Hanns Univ Dr Prof
Publication of CH182958A publication Critical patent/CH182958A/en

Links

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)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)

Description

  

      Verfahren    zur Darstellung eines neuen Esters der     2-Phenylchinolin-4-carbonsäure.       Es wurde gefunden, dass man durch     Ver-          esterung    des     Natriumsalzes    der     2-Phenylchi-          nolin-4-carbonsäure    mit     Glyzerin-a-dichlor-          hydrin    zu einer bisher nicht     beschriebenen     Verbindung gelangen kann, welche sowohl  therapeutische Anwendung, vornehmlich als       Antirheumaticum    und     Antiarthriticum,    fin  den kann,

   als auch ein     Zwischenprodukt    bei  Erlangung anderer, gleichfalls praktisch  brauchbarer Stoffe darstellt.  



  <I>Beispiel:</I>  30 Gewichtsteile     2-Phenylchinolin-4-car-          bonsaures    Natrium und 6,7 Gewichtsteile       Glyzerin-a-dichlorhydrin    werden 10 bis 20  Stunden auf     16'0    bis<B>170'</B> erhitzt. Dann wird  mit einer verdünnten     Lösung    von     Natrium-          carbonat    verrieben, mit Wasser neutral ge  waschen, mit Äther extrahiert und im Va  kuum getrocknet. Zwecks weiterer Reinigung  wird vorteilhaft in Olivenöl gelöst und mit       Petroläther    gefällt.

   Der so erhaltene     a,a'-Bis-          (2    -     phenylehinolin    - 4 -     carbonsäure)    -     glyze-          rinester    stellt ein, in den üblichen Alkoholen  leicht lösliches, in Wasser sehr schwer lös-         liches,    hell gefärbtes Kristallpulver dar, das  bei 58   schmilzt, geschmacklos ist und keinen  Geruch besitzt.



      Process for the preparation of a new ester of 2-phenylquinoline-4-carboxylic acid. It has been found that esterification of the sodium salt of 2-phenylquinoline-4-carboxylic acid with glycerol-a-dichlorohydrin can lead to a compound not previously described, which can be used both therapeutically, primarily as an anti-rheumatic and anti-arthritic, Can be found,

   as well as an intermediate product in obtaining other, equally practically useful substances.



  <I> Example: </I> 30 parts by weight of 2-phenylquinoline-4-carboxylic acid sodium and 6.7 parts by weight of glycerol-a-dichlorohydrin are 10 to 20 hours for 16'0 to <B> 170 '</B> heated. Then it is triturated with a dilute solution of sodium carbonate, washed neutral with water, extracted with ether and dried in vacuo. For further cleaning it is advantageous to dissolve it in olive oil and precipitate it with petroleum ether.

   The a, a'-bis- (2-phenylehinoline-4-carboxylic acid) -glycerin ester obtained in this way is a light-colored crystal powder which is easily soluble in the usual alcohols, very poorly soluble in water and melts at 58 , is tasteless and has no odor.

Claims (1)

PATENTANSPRUCH: Verfahren zur Darstellung -eines neuen Esters der 2-Phenylchinolin-4-carbonsäure, welcher ein hellgefärbtes, geschmack- und geruchloses, in Alkoholen leicht, in Wasser sehr schwer lösliches, bei 58 C schmelzendes kristallines Produkt darstellt, das in der Me dizin, vornehmlich als Antirheumaticum und Antiarthriticum Anwendung finden kann, dadurch gekennzeichnet, dass man das Natriumsalz der genannten Säure mit Glyze- rin-.a-dichlorhydrin verestert. PATENT CLAIM: Process for the preparation of a new ester of 2-phenylquinoline-4-carboxylic acid, which is a light-colored, tasteless and odorless, crystalline product which is easily soluble in alcohols, very sparingly soluble in water, melting at 58 C and which is used in medicine , primarily as an anti-rheumatic and anti-arthritic application, characterized in that the sodium salt of the acid mentioned is esterified with glycerine-α-dichlorohydrin. UNTERANSPRUCH: Verfahren nach Patentanspruch, dadurch gekennzeichnet, dass man die Veresterung durch Erhitzung der beiden Komponenten bei 160 bis 170 C durchführt. SUBSTANTIAL CLAIM: Process according to claim, characterized in that the esterification is carried out by heating the two components at 160 to 170 C.
CH182958D 1935-01-09 1935-01-09 Process for the preparation of a new ester of 2-phenylquinoline-4-carboxylic acid. CH182958A (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
CH182958T 1935-01-09

Publications (1)

Publication Number Publication Date
CH182958A true CH182958A (en) 1936-03-15

Family

ID=4431930

Family Applications (1)

Application Number Title Priority Date Filing Date
CH182958D CH182958A (en) 1935-01-09 1935-01-09 Process for the preparation of a new ester of 2-phenylquinoline-4-carboxylic acid.

Country Status (1)

Country Link
CH (1) CH182958A (en)

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