CH254449A - Process for the preparation of a new oxyhydrophenanthrene derivative. - Google Patents

Process for the preparation of a new oxyhydrophenanthrene derivative.

Info

Publication number
CH254449A
CH254449A CH254449DA CH254449A CH 254449 A CH254449 A CH 254449A CH 254449D A CH254449D A CH 254449DA CH 254449 A CH254449 A CH 254449A
Authority
CH
Switzerland
Prior art keywords
new
oxyhydrophenanthrene
derivative
preparation
tetrahydro
Prior art date
Application number
Other languages
German (de)
Inventor
Aktiengesellschaft Ciba
Original Assignee
Ciba 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 Ciba Geigy filed Critical Ciba Geigy
Publication of CH254449A publication Critical patent/CH254449A/en

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Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C62/00—Compounds having carboxyl groups bound to carbon atoms of rings other than six—membered aromatic rings and containing any of the groups OH, O—metal, —CHO, keto, ether, groups, groups, or groups
    • C07C62/30—Unsaturated compounds
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C69/00—Esters of carboxylic acids; Esters of carbonic or haloformic acids
    • C07C69/74—Esters of carboxylic acids having an esterified carboxyl group bound to a carbon atom of a ring other than a six-membered aromatic ring
    • C07C69/757—Esters of carboxylic acids having an esterified carboxyl group bound to a carbon atom of a ring other than a six-membered aromatic ring having any of the groups OH, O—metal, —CHO, keto, ether, acyloxy, groups, groups, or in the acid moiety

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

Description

  

  Verfahren zur Herstellung     eines    neuen     Oxyhydrophenanthren-Derivates.       Es     wurde    gefunden, dass man zu     einem     neuen     Oxyhydrophenanthren-Derivat    gelan  gen kann, wenn man einen 1-Äthyliden-2       methyl-7-oxy-1,2,3,4-tetrahydro-phenanthren-          2-carbonsäuremethylester    zwecks     Überfüh-          rung    der     Äthylidengruppierung    in einen       Äthylrest        mit    hydrierenden     Mitteln    behan  delt.  



  Für die Überführung der     Äthylidengrup-          pierung    in den     Äthylrest    kann     beispielsweise     die katalytische Hydrierung angewandt wer  den.  



  Das neue Verfahrensprodukt, der     1-Äthyl-          2        -methyl    -     7-oxy-,1,2,3,4-tetrahydro-phen-          anthren-2-carbonsäuremethylestervom.F.117      soll     therapeutische        Verwendung    finden oder  als Zwischenprodukt zur Herstellung thera  peutisch verwendbarer Verbindungen dienen.

         Beispiel:     1 Teil     1-Äthyliden-2-methyl-7-oxy-1,2,     3,4 -     tetrahydro    -     phenanthren    - 2 -     carb        onsäure-          methyles.ter    vom F. 209 bis 211  der Formel  
EMI0001.0032     
    (erhalten z.

   B. aus dem nach dem Verfahren  gemäss dem     @schweiz.    Hauptpatent Nr. 249115  erhältlichen 1- Äthyl-l-oxy-2-methyl-7-me-         thoxy-1,2,3,4        -tetrahydro-phenanthren-2-car-          bonsäuremethylester    vom F. 153  durch Was  serabspaltung     mittels    Ameisensäure oder Jod  in Chloroform und anschliessender     Spaltung     der     7-Methoxy-Gruppe    durch Erhitzen mit       Pyridinhydrochlorid)        wird    in 30 Teilen Al  kohol in Gegenwart von Platinoxyd unter  Wasserstoff geschüttelt.

   Nach     Aufnahme    der  für 1     Moläquivalent    berechneten Menge Was  serstoff wird die Lösung vom     Katalysator          abfiltriert    und eingedampft. Durch     Umkri-          stallisieren    des Rückstandes aus verdünntem  Methylalkohol erhält man den     1-Äthyl-2-me-          thyl    -     7-oxy-1,2,3,4-tetrahydro-phenanthren-2-          carbonsäuremethylester    der Formel  
EMI0001.0052     
    in Form glänzender Blättchen vom F. 117 .  Die Hydrierung kann auch in Eisessig in  Gegenwart von     Palladium-Tierkohle    vorge  nommen werden.



  Process for the preparation of a new oxyhydrophenanthrene derivative. It has been found that a new oxyhydrophenanthrene derivative can be obtained if a 1-ethylidene-2-methyl-7-oxy-1,2,3,4-tetrahydro-phenanthrene-2-carboxylic acid methyl ester is used for the purpose of transferring the Ethylidene grouping in an ethyl radical treated with hydrogenating agents.



  Catalytic hydrogenation, for example, can be used to convert the ethylidene group into the ethyl radical.



  The new process product, the 1-ethyl-2-methyl-7-oxy-, 1,2,3,4-tetrahydro-phen-anthrene-2-carboxylic acid methyl ester from F.117 is intended to be used therapeutically or as an intermediate product for preparation usable connections.

         Example: 1 part of 1-ethylidene-2-methyl-7-oxy-1,2,3,4 - tetrahydro - phenanthrene - 2 - carbonic acid methyles.ter of F. 209 to 211 of the formula
EMI0001.0032
    (received e.g.

   B. from the procedure according to @schweiz. Main patent no. 249115 available 1- ethyl-l-oxy-2-methyl-7-methoxy-1,2,3,4-tetrahydro-phenanthrene-2-carboxylic acid methyl ester from F. 153 by splitting off water with formic acid or Iodine in chloroform and subsequent cleavage of the 7-methoxy group by heating with pyridine hydrochloride) is shaken under hydrogen in 30 parts of alcohol in the presence of platinum oxide.

   After taking up the amount of hydrogen calculated for 1 molar equivalent, the solution is filtered off from the catalyst and evaporated. By recrystallizing the residue from dilute methyl alcohol, 1-ethyl-2-methyl-7-oxy-1,2,3,4-tetrahydro-phenanthrene-2-carboxylic acid methyl ester of the formula is obtained
EMI0001.0052
    in the form of shiny leaves from F. 117. The hydrogenation can also be carried out in glacial acetic acid in the presence of palladium animal charcoal.

Claims (1)

PATENTANSPRUCH: Verfahren zur Herstellung eines neuen Oxyhydrophenanthren-Derivates, dadurch ge kennzeichnet, dass man einen 1-Äthyliden-2 methyl-7-oxy-1,2,3,4-tetrahydro-phenanthren- 2-carbonsäuremethylester zwecks Überfüh rung der Äthylidengruppierung in einen Äthylrest mit hydrierenden Mitteln behan delt. PATENT CLAIM: A process for the preparation of a new oxyhydrophenanthrene derivative, characterized in that a 1-ethylidene-2-methyl-7-oxy-1,2,3,4-tetrahydro-phenanthrene-2-carboxylic acid methyl ester is used to convert the ethylidene group into an ethyl residue treated with hydrogenating agents. Das. neue Verfahrensprodukt, der 1- Äthyl - 2 - methyl - 7 - ogy-1,2,3,4-tetrahydro- phenanthren-2-carbonsäuremethylester vom F. l17 soll therapeutische Verwendung fin den-. oder _ als Zwisehenprodukt zur, Herstel lung therapeutisch verwendbarer Verbindun gen dienen. The. new process product, the 1-ethyl-2-methyl-7-ogy-1,2,3,4-tetrahydro- phenanthrene-2-carboxylic acid methyl ester from F. l17 is to be used in therapy. or _ serve as an intermediate product for the production of therapeutically usable compounds. _ . UNTERANSPRüCHE 1. 'Verfahren gemäss Patentanspruch, da durch gekennzeichnet, dass man die Hydrie rung mittels katalytisch angeregtem Wasser stoff vornimmt. 2. Verfahren gemäss Patentanspruch, da durch .gekennzeichnet; -dass-ma-R--die Hydrie rung in Eisessig in Gegenwart.von Palla- dium-Tierkohle vornimmt. _. SUBClaims 1. Process according to patent claim, characterized in that the hydrogenation is carried out by means of catalytically activated hydrogen. 2. Method according to claim, as marked by; -that-ma-R - carries out the hydrogenation in glacial acetic acid in the presence of palladium animal charcoal.
CH254449D 1944-01-10 1944-01-10 Process for the preparation of a new oxyhydrophenanthrene derivative. CH254449A (en)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
CH254449T 1944-01-10
CH242609T 1944-01-10

Publications (1)

Publication Number Publication Date
CH254449A true CH254449A (en) 1948-04-30

Family

ID=25728717

Family Applications (1)

Application Number Title Priority Date Filing Date
CH254449D CH254449A (en) 1944-01-10 1944-01-10 Process for the preparation of a new oxyhydrophenanthrene derivative.

Country Status (1)

Country Link
CH (1) CH254449A (en)

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