CH254452A - Process for the preparation of a new oxyhydrophenanthrene derivative. - Google Patents

Process for the preparation of a new oxyhydrophenanthrene derivative.

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Publication number
CH254452A
CH254452A CH254452DA CH254452A CH 254452 A CH254452 A CH 254452A CH 254452D A CH254452D A CH 254452DA CH 254452 A CH254452 A CH 254452A
Authority
CH
Switzerland
Prior art keywords
new
preparation
phenanthrene
carboxylic acid
methyl ester
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 CH254452A publication Critical patent/CH254452A/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-Der@vä.t    gelan  gen kann, wenn man     einen        1-Äthyliden-2-me-          thyl    - 7     --benzoyloxy        -1,2,3,

  4-tetrahydro-phen-          anthren    - 2 -     carbonsäuremethylester    zwecks       überführung    der     Äthylidengruppierung        in     einen     Äthylrest        mit        hydrolysierenden    Mit  teln     behandelt.     



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



  Das, neue     Verfahrensprodukt,    der     1-Athyl-          2        -rnethyl-    7     -benzoyloxy-1,2,3,4-tetrahydro-          phenanthren-2-carbonsäuremethylester    vom  F. 130 bis     132 ,    soll     therapeutische    Verwen  dung finden oder als Zwischenprodukt zur  Herstellung therapeutisch verwendbarer Ver  bindungen dienen.  



       Beispiel:     1 Teil 1-     Athyliden    - 2 -     methyl-7-benzoyl-          oxy-1,2,3,4        ;tetrahydro-phenanthren-2-carbon-          säuremethylester    der Formel  
EMI0001.0038     
    (erhalten z. B. aus dem nach dem Verfahren  gemäss dem Schweiz.

   Hauptpatent Nr. 249115  erhältlichen 1- Äthyl -1-     oxy-2    - methyl-7-me-         thoxy        -,    1,2, 3,4     =-tetrahydrophenanthren-        2-car-          bonsäuremethylester    vom     F''.153     durch     Was-          serabspaltung        mittels    Ameisensäure oder Jod       in        Chloroform,

      Spaltung der     7-Methoxy     Gruppe durch     Erhitzen    mit     Pyridinhydro-          chlorid    und     anschliessende        Veresterung    mit       Benzoylchlorid    und     Pyridin)        wird    in 30 Tei  len Alkohol     in    Gegenwart von Platinoxyd  unter Wasserstoff geschüttelt.

   Nach Auf  nahme der für 1     Moläquivalent    berechneten  Menge     Wasserstoff    wird     die    Lösung vom       .Katalysator        abfiltriert    und     eingedampft.     Durch     Umkristallisieren    des Rückstandes aus       verdünntem    Methylalkohol erhält man den       1-Athyl-2-methyl-7-benzoyloxy-1,2,3,4-tetra-          hydro-phenanthren-24.oarbonsäureme'thylester     der Formel  
EMI0001.0071     
    in Form farbloser Kristalle vom F. 130 bis  132 .  



  Die Hydrierung kann auch     in    Eisessig in  Gegenwart von     Palladium-Tierkohle    vorge  nommen werden.



  Process for the preparation of a new oxyhydrophenanthrene derivative. It was "found that you can get to a new Oxyhydrophenanthren-Der@vä.t if you use a 1-ethylidene-2-methyl-7 -benzoyloxy -1,2,3,

  4-tetrahydro-phenanthrene - 2 - carboxylic acid methyl ester treated with hydrolyzing agents for the purpose of converting the ethylidene group into an ethyl radical.



  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-benzoyloxy-1,2,3,4-tetrahydro- phenanthrene-2-carboxylic acid methyl ester of 130 to 132, should find therapeutic use or as an intermediate for production Use therapeutically usable compounds.



       Example: 1 part 1-ethylidene - 2 - methyl-7-benzoyl-oxy-1,2,3,4; tetrahydro-phenanthrene-2-carboxylic acid methyl ester of the formula
EMI0001.0038
    (obtained e.g. from the procedure according to Switzerland.

   Main patent No. 249115 available 1-ethyl-1-oxy-2-methyl-7-methoxy-, 1,2, 3,4 = -tetrahydrophenanthrene-2-carboxylic acid methyl ester of F ". 153 by splitting off water using formic acid or iodine in chloroform,

      Cleavage of the 7-methoxy group by heating with pyridine hydrochloride and subsequent esterification with benzoyl chloride and pyridine) is shaken in 30 parts of alcohol in the presence of platinum oxide under hydrogen.

   After taking up the amount of hydrogen calculated for 1 molar equivalent, the solution is filtered off from the catalyst and evaporated. Recrystallization of the residue from dilute methyl alcohol gives methyl 1-ethyl-2-methyl-7-benzoyloxy-1,2,3,4-tetrahydro-phenanthrene-24-carboxylate of the formula
EMI0001.0071
    in the form of colorless crystals from F. 130 to 132.



  The hydrogenation can also be carried out in glacial acetic acid in the presence of palladium charcoal.

Claims (1)

PATENTANSPRUCH: Verfahren zur Herstellung einen. neuen Oxyhydrophenanthren-D'erivates, dadurch ge kennzeichnet, dass man einen 1-Äthyliden-2 methyl-7-benzoyloxy-1,2,3,4-tetrahydro-phen- anthren - 2 - carbonsäuremethylester zwecks überführung der Äthylidengruppierung in einen Äthylrest mit hydrierenden Mitteln be handelt. PATENT CLAIM: Process for producing a. new Oxyhydrophenanthren-D'erivates, characterized in that a 1-ethylidene-2-methyl-7-benzoyloxy-1,2,3,4-tetrahydro-phenanthrene-2 - carboxylic acid methyl ester for the purpose of converting the ethylidene group into an ethyl radical with hydrogenating agents. Das neue Verfahrensprodukt, der. 1-Äthyl- 2 -methy1- T-benzoylogy -1,2,3,4-@etrahydro- phenanthren-2-carbonsäuremethylester vom F. 130 bis 132 , soll therapeutische Verwen dung finden oder als Zwischenprodukt zur Herstellung therapeutisch verwendbarer Ver bindung dienen. UNTERANSPRÜCHE: 1.. The new process product, the. 1-Ethyl- 2 -methy1- T-benzoylogy -1,2,3,4- @ etrahydro- phenanthrene-2-carboxylic acid methyl ester from F. 130 to 132, should find therapeutic use or serve as an intermediate for the preparation of therapeutically useful compounds . SUBCLAIMS: 1 .. Verfahren gemäss Pätentanspruch, da durch gekennzeichnet, dass man die Hydrie rung nvtteIs katalytisch angeregtem Wasser stoff vornimmt. 2. Verfahren gemäss Patentanspruch, da durch gekennzeichnet, dass man' die Hydrie rung in Eisessig in Gegenwart- von Palla- dinm-Tierkohle vornimmt, Method according to the patent claim, characterized in that the hydrogenation is carried out using catalytically activated hydrogen. 2. The method according to claim, characterized in that 'the hydrogenation is carried out in glacial acetic acid in the presence of palladium animal charcoal,
CH254452D 1944-01-10 1944-01-10 Process for the preparation of a new oxyhydrophenanthrene derivative. CH254452A (en)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
CH254452T 1944-01-10
CH242609T 1944-01-10

Publications (1)

Publication Number Publication Date
CH254452A true CH254452A (en) 1948-04-30

Family

ID=25728720

Family Applications (1)

Application Number Title Priority Date Filing Date
CH254452D CH254452A (en) 1944-01-10 1944-01-10 Process for the preparation of a new oxyhydrophenanthrene derivative.

Country Status (1)

Country Link
CH (1) CH254452A (en)

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