CH262164A - Process for the preparation of a new oxyhydrophenanthrene derivative. - Google Patents

Process for the preparation of a new oxyhydrophenanthrene derivative.

Info

Publication number
CH262164A
CH262164A CH262164DA CH262164A CH 262164 A CH262164 A CH 262164A CH 262164D A CH262164D A CH 262164DA CH 262164 A CH262164 A CH 262164A
Authority
CH
Switzerland
Prior art keywords
new
derivative
preparation
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 CH262164A publication Critical patent/CH262164A/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     Oxyhy        droplienanthren-Derivat    gelan  gen kann, wenn man     1-Äthyliden-2-n-propyl-          7-methoxy    -1,2,3,4     -tetrahydro    -     phenanthren-2-          carbonsäure-methylester    zwecks     Überführung     der     Äthylidengruppierung    in einen     Äthylrest     mit hydrierenden Mitteln behandelt.  



  Für die Überführung der     Äthylidengrup-          pierung    in den     Äthy        lrest    kann beispielsweise  die katalytische Hydrierung dienen.    Das neue Verfahrensprodukt, der     1-Äthyl-          2-n-propyl-7-metlioxy-1,2,3,4-tetrahydro    -     phen-          anthren-2-carbonsäure-inetliylester    vorn F.111  bis 112 , soll therapeutische Verwendung  finden oder als Zwischenprodukt zur Her  stellung therapeutisch verwendbarer Verbin  dungen dienen.

      <I>Beispiel:</I>    1 Teil 1- Ätliyiiden-2-n-propyl-7-methoxy       1,2,3,4-tetraliydro-phenanthren-2-earbonsäure-          methylester    der Formel  
EMI0001.0022     
    (erhalten z. B. aus dem gemäss dem     schweiz.     Patent Nr. 254454 erhältlichen     1-Äthyl-1-oxy-          2-n-propy        1-7-nietlioxy-1,2,3,4-tetrahydro    -     phen-          anthren-2-carbonsäure-methylester    vom F.127  bis 128  durch Wasserabspaltung mittels    Ameisensäure oder Jod in Chloroform) wird  in 30 Teilen Alkohol in Gegenwart von Pla  tinoxyd unter Wasserstoff geschüttelt.

   Nach  Aufnahme der für 1     Moläquivalent    berech  neten Menge Wasserstoff wird die Lösung  vom Katalysator     abfiltriert    und eingedampft.  Durch     Umkristallisieren    des Rückstandes aus  verdünntem Methylalkohol erhält man den  1- Äthyl - 2 - n -     propyl-7-methoxy-1,2,3,4    -     tetra-          hydro-phenanthren-2-carbonsäure-methylester     der Formel  
EMI0001.0035     
    in Form derber Kristalle vom F. 111 bis 112 .    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 Oxyhy droplienanthren derivative can gelan conditions if 1-ethylidene-2-n-propyl-7-methoxy -1,2,3,4-tetrahydro - phenanthrene-2-carboxylic acid methyl ester treated with hydrogenating agents for the purpose of converting the ethylidene group into an ethyl radical.



  Catalytic hydrogenation, for example, can serve to convert the ethylidene group into the ethyl residue. The new process product, the 1-ethyl-2-n-propyl-7-metlioxy-1,2,3,4-tetrahydro - phen-anthrene-2-carboxylic acid inetliylester from F.111 to 112, is to be used or serve as an intermediate for the preparation of therapeutically usable compounds.

      <I> Example: </I> 1 part 1-Ätliyiiden-2-n-propyl-7-methoxy 1,2,3,4-tetraliydro-phenanthrene-2-carboxylic acid methyl ester of the formula
EMI0001.0022
    (obtained e.g. from the 1-ethyl-1-oxy-2-n-propy 1-7-nietlioxy-1,2,3,4-tetrahydro-phen-anthrene- Methyl 2-carboxylate from F.127 to 128 by elimination of water by means of formic acid or iodine in chloroform) is shaken in 30 parts of alcohol in the presence of platinum oxide under hydrogen.

   After the amount of hydrogen calculated for 1 molar equivalent has been taken up, the solution is filtered off from the catalyst and evaporated. Recrystallization of the residue from dilute methyl alcohol gives 1-ethyl-2-n-propyl-7-methoxy-1,2,3,4-tetrahydro-phenanthrene-2-carboxylic acid methyl ester of the formula
EMI0001.0035
    in the form of coarse crystals from F. 111 to 112. 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 1-äthy liden-2-n-propy 1- 7-methoxy-1,2,3,4-tetrahydro- phenanthren-2- earbonsäure-methylester zwecks Überführung der Äthy lidengruppierung in einen Äthy lrest mit hydrierenden Mitteln behandelt. Claim: Process for the preparation of a new Oxyhydrophenanthren derivative, characterized in that 1-ethy liden-2-n-propy 1- 7-methoxy-1,2,3,4-tetrahydrophenanthrene-2-carboxylic acid methyl ester treated with hydrogenating agents for the purpose of converting the Äthy lidengruppierung in an Äthy lrest. Das neue Verfahrensprodukt, der 1-Äthyl 2-n-propyl-7-methox3>-1,2,3,4-tetrahydro-phen- anthren-2-carbonsäure-methylester vom F.117 bis 112 , soll therapeutische Verwendung finden oder als Zwischenprodukt nur Herstel lung therapeutisch verwendbarer Verbindun- gen dienen. UNTERANSPRUCH: The new process product, the 1-ethyl 2-n-propyl-7-methox3> -1,2,3,4-tetrahydro-phen-anthrene-2-carboxylic acid methyl ester from F.117 to 112, is to find therapeutic use or only serve as an intermediate product for the production of therapeutically usable compounds. SUBClaim: Verfahren gemäss Patentanspruch, dadurch gekennzeichnet, dass man die Hydrierung in Eisessig in Gegenwart von Palladium-Tier- kohle vornimmt. Process according to patent claim, characterized in that the hydrogenation is carried out in glacial acetic acid in the presence of palladium charcoal.
CH262164D 1944-01-10 1944-01-10 Process for the preparation of a new oxyhydrophenanthrene derivative. CH262164A (en)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
CH262164T 1944-01-10
CH242609T 1944-01-10

Publications (1)

Publication Number Publication Date
CH262164A true CH262164A (en) 1949-06-15

Family

ID=25728723

Family Applications (1)

Application Number Title Priority Date Filing Date
CH262164D CH262164A (en) 1944-01-10 1944-01-10 Process for the preparation of a new oxyhydrophenanthrene derivative.

Country Status (1)

Country Link
CH (1) CH262164A (en)

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