CH262163A - Process for the preparation of a new oxyhydrophenanthrene derivative. - Google Patents

Process for the preparation of a new oxyhydrophenanthrene derivative.

Info

Publication number
CH262163A
CH262163A CH262163DA CH262163A CH 262163 A CH262163 A CH 262163A CH 262163D A CH262163D A CH 262163DA CH 262163 A CH262163 A CH 262163A
Authority
CH
Switzerland
Prior art keywords
new
preparation
derivative
tetrahydro
methoxy
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 CH262163A publication Critical patent/CH262163A/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

Landscapes

  • 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     1-Äthyliden-2-äthyl-          7-methoxy    -1,2,3,4 -     tetrahydro    -     phenanthren-2-          earbonsäure-methylester    zwecks Überführung  -der     Äthylidengruppierung    in einen     Äthylrest     mit hydrierenden Mitteln behandelt.  



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



  Das neue Verfahrensprodukt, der     1,2-Di-          äthyl    - 7 -     methoxy    -1,2,3,4 -     tetrahydro    -     phen-          anthren-2-carbonsäure-methylester    vom F. 69  bis 70 , soll therapeutische Verwendung fin  den oder als Zwischenprodukt zur Herstel  lung therapeutisch verwendbarer Verbindun  gen dienen.  



  <I>Beispiel:</I>  1 Teil 1-     Äthyliden    - 2 -     äthyl    - 7 -     methoxy-          1,2,3,4-tetrahydro        -phenanthren-2-carbonsäure-          methylester    der Formel  
EMI0001.0025     
    (erhalten z.

   B. aus dem gemäss dem     sehweiz.     Patent Nr. 254453 erhältlichen     1-Äthyl-l-oxy-          2    -     äthyl    -'7 -     methoxy    -1,2, 3,4 -     tetrahy        dro    -     phen-          anthren-2-carbonsäure-methylester    vom F.131  bis 132  durch Wasserabspaltung mittels    Ameisensäure oder Jod in Chloroform) wird  in 30 Teilen     Alkohol.    in Gegenwart von Platin  oxyd und 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     1,2-          Diäthyl    - 7 -     methoxy-1,2,3,4        -tetrahydro    -     phen-          anthren-2-earbonsäure-methylester    der Formel  
EMI0001.0045     
    in Form derber Kristalle vom F. 69 bis 70 .  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 gelan conditions if 1-ethylidene-2-ethyl- 7-methoxy -1,2,3,4 - tetrahydro - phenanthrene-2-carboxylic acid methyl ester for the purpose of conversion - the ethylidene group in an ethyl residue 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 1,2-diethyl-7-methoxy -1,2,3,4-tetrahydro-phenanthrene-2-carboxylic acid methyl ester from 69 to 70, is to be used in therapy or as Intermediate product for the production of therapeutically usable compounds.



  <I> Example: </I> 1 part 1-ethylidene-2-ethyl-7-methoxy-1,2,3,4-tetrahydro-phenanthrene-2-carboxylic acid methyl ester of the formula
EMI0001.0025
    (received e.g.

   B. from the according to the Sehweiz. Patent No. 254453 available 1-ethyl-1-oxy-2-ethyl -'7-methoxy-1,2,3,4-tetrahydro-phen-anthrene-2-carboxylic acid methyl ester from F.131 to 132 by elimination of water using formic acid or iodine in chloroform) becomes alcohol in 30 parts. Shaken in the presence of platinum oxide and hydrogen.

   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, the 1,2-diethyl-7-methoxy-1,2,3,4-tetrahydro-phenanthrene-2-carboxylic acid methyl ester of the formula is obtained
EMI0001.0045
    in the form of coarse crystals from 69 to 70. 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 gekennzeichnet, dass man 1-Äthyliden-2-äthyl- 7 - methoxy -1,2,3,4 - tetrahydro-phenanthren-2- carbonsäure-methylester zwecks Überführung der Äthylidengruppierung in einen Äthylrest mit hydrierenden Mitteln behandelt. PATENT CLAIM: Process for the preparation of a new Oxyhydrophenanthren - derivative, characterized in that 1-ethylidene-2-ethyl- 7-methoxy -1,2,3,4-tetrahydro-phenanthrene-2-carboxylic acid methyl ester for the purpose of converting the ethylidene group into treated an ethyl residue with hydrogenating agents. Das neue Verfahrensprodukt, der 1,2-Di- äthyl - 7 - methoxy -1,2,3,4 - tetrahydro - phen- anthren-2-carbonsäure-methylester vom F.69 bis 70 , soll therapeutische Verwendung fin den oder als Zwischenprodukt zur Herstel lung therapeutischverwendbarerVerbindungen dienen. UNTERANSPRUCH: Verfahren gemäss Patentanspruch, dadurch. gekennzeichnet, dass man die Hydrierung in Eisessig in Gegenwart von Palladium-Tier- kohle vornimmt. The new process product, the 1,2-diethyl-7-methoxy -1,2,3,4-tetrahydro-phenanthrene-2-carboxylic acid methyl ester from F.69 to 70, is to be used in therapy or as Serve intermediate product for the preparation of therapeutically useful compounds. SUBClaim: Method according to claim, thereby. characterized in that the hydrogenation is carried out in glacial acetic acid in the presence of palladium charcoal.
CH262163D 1944-01-10 1944-01-10 Process for the preparation of a new oxyhydrophenanthrene derivative. CH262163A (en)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
CH242609T 1944-01-10
CH262163T 1944-01-10

Publications (1)

Publication Number Publication Date
CH262163A true CH262163A (en) 1949-06-15

Family

ID=25728722

Family Applications (1)

Application Number Title Priority Date Filing Date
CH262163D CH262163A (en) 1944-01-10 1944-01-10 Process for the preparation of a new oxyhydrophenanthrene derivative.

Country Status (1)

Country Link
CH (1) CH262163A (en)

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