CH297657A - Process for the preparation of a 3-substituted 4-oxycoumarin. - Google Patents

Process for the preparation of a 3-substituted 4-oxycoumarin.

Info

Publication number
CH297657A
CH297657A CH297657DA CH297657A CH 297657 A CH297657 A CH 297657A CH 297657D A CH297657D A CH 297657DA CH 297657 A CH297657 A CH 297657A
Authority
CH
Switzerland
Prior art keywords
sep
substituted
oxycoumarin
oxy
preparation
Prior art date
Application number
Other languages
German (de)
Inventor
Ag J R Geigy
Original Assignee
Ag J R Geigy
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 Ag J R Geigy filed Critical Ag J R Geigy
Publication of CH297657A publication Critical patent/CH297657A/en

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Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D311/00—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only hetero atom, condensed with other rings
    • C07D311/02—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only hetero atom, condensed with other rings ortho- or peri-condensed with carbocyclic rings or ring systems
    • C07D311/04—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring
    • C07D311/42—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring with oxygen or sulfur atoms in positions 2 and 4
    • C07D311/44—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring with oxygen or sulfur atoms in positions 2 and 4 with one hydrogen atom in position 3
    • C07D311/46—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring with oxygen or sulfur atoms in positions 2 and 4 with one hydrogen atom in position 3 unsubstituted in the carbocyclic ring

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Pyrane Compounds (AREA)
  • Plural Heterocyclic Compounds (AREA)

Description

  

  Verfahren zur Herstellung eines     3-substituierten        4-Oxy-eumarins.     
EMI0001.0003     
  
    Gegenstand <SEP> vorliegenden <SEP> Patentes <SEP> ist <SEP> ein
<tb>  Verfahren <SEP> zur <SEP> Herstellung <SEP> eines <SEP> 3-subst.ituier  ten <SEP> 4-Oxy-cumarins. <SEP> Das <SEP> Verfahren <SEP> ist <SEP> da  dureh <SEP> gekennzeiehnet, <SEP> dass <SEP> man <SEP> 4-Brom-ben  z;tl-aeetoii <SEP> auf <SEP> 4-Oxy-cunia.rin <SEP> einwirken <SEP> lässt.

         Die erhaltene     neueVerbindung,    das     3-[a-(4'-          Brom-pheny        1)-fl-aceti-l-äthy    1] -     4-oxy-        cumarin,     zeigt einen Schmelzpunkt von     1.64-166 .    Sie       soll        als        P        toclentizid        Verwendung        finden.            Beispiel:

         16 Teile     4-Oxy-eumarin        und        ?\?,5    Teile       4-Bi,om-lienzalaceton    werden in 75 Teilen       Py        riclin        ?4    Stunden. unter     Rüchfluss    gekocht.  Dann liesst man die erhaltene Lösung in       Nasser,        versetzt    mit Salzsäure bis     znr    kongo  sauren Reaktion und trennt. die wässerige  Flüssigkeit vom harzigen Reaktionsprodukt.    Dieses wird mit Wasser gewaschen, ge  trocknet und aus verdünntem Methanol um  kristallisiert.  



  Man erhält     3-[a-(4'-Brom-phenyl)-fl-ace-          tyl-äthyl]-4-oxy-eumarin    vom     Smp.    164 bis  166 .  



  Anstatt in     Pvridin    kann man die     Uniset-          zung    zum Beispiel auch in Wasser oder in       Dioxan,    welchem wenig     Piperidin    zugefügt  ist. ausführen.



  Process for the preparation of a 3-substituted 4-oxy-eumarin.
EMI0001.0003
  
    The subject of <SEP> present <SEP> patent <SEP> is <SEP> a
<tb> Process <SEP> for the <SEP> production <SEP> of a <SEP> 3-substituted <SEP> 4-oxycoumarin. <SEP> The <SEP> method <SEP> is <SEP> because <SEP> marked, <SEP> that <SEP> man <SEP> 4-bromine ben z; tl-aeetoii <SEP> on <SEP> Lets 4-Oxy-cunia.rin <SEP> take effect <SEP>.

         The new compound obtained, 3- [a- (4'-bromo-pheny 1) -fl-aceti-1-ethy 1] -4-oxycoumarin, has a melting point of 1.64-166. It is said to be used as a p toclenticide. Example:

         16 parts of 4-oxy-eumarin and? \ ?, 5 parts of 4-bi, om-lienzalacetone are in 75 parts of py riclin? For 4 hours. cooked under reflux. The solution obtained is then left in water, hydrochloric acid is added until the reaction is acidic to the Congo, and the mixture is separated. the aqueous liquid from the resinous reaction product. This is washed with water, dried and crystallized from dilute methanol.



  3- [a- (4'-Bromo-phenyl) -fl-acetyl-ethyl] -4-oxy-eumarin of melting point 164 to 166 is obtained.



  Instead of pvridine, the solution can also be used, for example, in water or in dioxane to which little piperidine has been added. To run.

Claims (1)

PATENTANSPRUCH: Verfahren zur Herstellung eines 3-substi- tuierten 4-Oxy-cumarins, dadurch gekenn zeichnet, dass man 4-Brom-benzalaceton auf 4-Oxy-cumarin einwirken lässt. Die erhaltene neue Verbindung, das 3-1=a-(4'- Brom-phenyl) -ss-a cetyl-äthvl ] - 4-oxy - cumar in, zeigt einen Schmelzpunkt von 164-166 . PATENT CLAIM: Process for the production of a 3-substituted 4-oxy-coumarin, characterized in that 4-bromo-benzalacetone is allowed to act on 4-oxy-coumarin. The new compound obtained, the 3-1 = a- (4'-bromo-phenyl) -ss-a cetyl-ether] -4-oxy-coumarin, has a melting point of 164-166.
CH297657D 1950-01-31 1950-01-31 Process for the preparation of a 3-substituted 4-oxycoumarin. CH297657A (en)

Applications Claiming Priority (3)

Application Number Priority Date Filing Date Title
CH701111X 1950-01-31
CH297657T 1950-01-31
CH289578T 1950-07-25

Publications (1)

Publication Number Publication Date
CH297657A true CH297657A (en) 1954-03-31

Family

ID=27178171

Family Applications (1)

Application Number Title Priority Date Filing Date
CH297657D CH297657A (en) 1950-01-31 1950-01-31 Process for the preparation of a 3-substituted 4-oxycoumarin.

Country Status (1)

Country Link
CH (1) CH297657A (en)

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