CH254448A - Process for the preparation of a new oxyhydrophenanthrene derivative. - Google Patents

Process for the preparation of a new oxyhydrophenanthrene derivative.

Info

Publication number
CH254448A
CH254448A CH254448DA CH254448A CH 254448 A CH254448 A CH 254448A CH 254448D A CH254448D A CH 254448DA CH 254448 A CH254448 A CH 254448A
Authority
CH
Switzerland
Prior art keywords
new
derivative
preparation
carboxylic acid
propylidene
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 CH254448A publication Critical patent/CH254448A/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-Propyliden-2-          methyl-    7     -methoxy-1,2,3,4-tetrahydro-phen-          anthren-2-carbonsäuremethylester    zwecks  Überführung der     Propylidengruppierung    in  einen     Propylrest    mit hydrierenden Mitteln  behandelt.

      Für die     Überführung    der     Propyliden-          grüppierung    in den     Propylrest    kann bei  spielsweise die katalytische Hydrierung an  gewandt werden.  



  Das neue Verfahrensprodukt, der     1-Pro-          pyl-2#,methyl-7-methoxy-1,2,3,4        ;tetrahydro-          phenanthren-2-carbonsäuremethylester    vom       Sdp.        o,oz        ",    180 , soll therapeutische Verwen  dung finden oder als Zwischenprodukt zur       Herstellung    therapeutisch verwendbarer Ver  bindungen dienen.         Beispiel:     1 Teil 1-Propyliden-2-methyl-7-methoxy       1,2,3,4-tetrahydrophenanthren-2-carbonsäure-          methylester    der Formel  
EMI0001.0025     
    (erhalten z.

   B. aus dem analog dem Verfah  ren des.     schweiz.        Hauptpatentes-    Nr. 249115    erhältlichen 1-     Propyl        -1-oxy-2-methyl-7-me-          thoxy        H        1',2,3,41-'.tetrahydro-phenanthren.-2-car-          bonsäuremethylester    durch     Wasserabspaltung          mittels    Ameisensäure oder Jod in Chloro  form)     wird    in 30 Teilen Alkohol in Gegen  wart von     Platinoxyd    unter     Wasserstoff    ge  schüttelt.

   Nach Aufnahme der für 1     Moläqui-          valent    berechneten Menge     Wasserstoff        wird     die Lösung vom Katalysator     abfiltriert        und     eingedampft.

   Durch     Destillation    des     R,ück-          standes    im Hochvakuum erhält man den       1-Propyl    - 2     -methyl    -     7-metJioxy-1,2,3,4-tetra-          hydro-phenanthren-2-carbonsäure-methylester     der Formel  
EMI0001.0052     
    in Form     eines    farblosen Öls vom     Sdp.        o,oZ    mm  180 .    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-propylidene-2-methyl-7-methoxy-1,2,3,4-tetrahydro-phenanthrene-2-carboxylic acid methyl ester is used for conversion treated the propylidene group in a propyl radical with hydrogenating agents.

      Catalytic hydrogenation, for example, can be used to convert the propylidene grouping into the propyl radical.



  The new product of the process, the 1-propyl-2 #, methyl-7-methoxy-1,2,3,4; tetrahydro- phenanthrene-2-carboxylic acid methyl ester of bp. O, oz ", 180, is to find therapeutic use or serve as an intermediate product for the preparation of therapeutically useful compounds Example: 1 part of 1-propylidene-2-methyl-7-methoxy 1,2,3,4-tetrahydrophenanthrene-2-carboxylic acid methyl ester of the formula
EMI0001.0025
    (received e.g.

   B. from the analogous to the procedural ren des. Switzerland. Main patent No. 249115 available 1-propyl -1-oxy-2-methyl-7-methoxy H 1 ', 2,3,41 -'. Tetrahydro-phenanthrene-2-carboxylic acid methyl ester by elimination of water with formic acid or Iodine in chloro form) is shaken under hydrogen in 30 parts of alcohol in the presence of platinum oxide.

   After the amount of hydrogen calculated for 1 molar equivalent has been taken up, the solution is filtered off from the catalyst and evaporated.

   Distilling the residue in a high vacuum gives the 1-propyl-2-methyl-7-methoxy-1,2,3,4-tetrahydrophenanthrene-2-carboxylic acid methyl ester of the formula
EMI0001.0052
    in the form of a colorless oil of bp o, oZ mm 180. 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-Propyliden- 2-methyl-7-methoxy-1, 2, 3,4- tetrahydro-phen- anthren - 2 - carbonsäuremethylester zwecks Überführung der Propylidengruppierung in einen Propylrest mit hydrierenden Mitteln beliandelt. Das neue Verfahrensprodukt, PATENT CLAIM: Process for the preparation of a new Oxyhydrophenanthren derivative, characterized in that a 1-propylidene-2-methyl-7-methoxy-1, 2, 3,4-tetrahydro-phen-anthrene - 2 - carboxylic acid methyl ester for the purpose of conversion Propylidene grouping into a propyl radical with hydrogenating agents. The new process product, der 1-Pxopyl- 2-methyl-7-methogy-1, 2, 3,4- tetrahydro-phen- anthren-2-carbonsäuremethylester vom Sdp. o,o@ mm 180 , soll therapeutische Verwendung finden oder als Zwischenprodukt zur Her stellung therapeutisch verwendbarer Verbin dungen dienen. UNTERANSPRüCHE 1. 1-Pxopyl-2-methyl-7-methogy-1, 2, 3,4-tetrahydro-phen-anthrene-2-carboxylic acid methyl ester with a bp. o, o @ mm 180, is intended to be used therapeutically or as an intermediate for manufacture Serve therapeutically usable connec tions. SUBCLAIMS 1. Verfahren gemäss Patentanspruch, da durch gekennzeichnet, dass man die Hydrie rung mittele katalytisch angeregtem Wasser stoff vornimmt. 2. Verfahren gemäss Patentanspruch, da durch gekennzeichnet, dass man die Hydrie rung in Eisessig in Gegenwart von Palla- dium-Tierkohle vornimmt. Process according to patent claim, characterized in that the hydrogenation is carried out by means of 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.
CH254448D 1944-01-10 1944-01-10 Process for the preparation of a new oxyhydrophenanthrene derivative. CH254448A (en)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
CH242609T 1944-01-10
CH254448T 1944-01-10

Publications (1)

Publication Number Publication Date
CH254448A true CH254448A (en) 1948-04-30

Family

ID=25728716

Family Applications (1)

Application Number Title Priority Date Filing Date
CH254448D CH254448A (en) 1944-01-10 1944-01-10 Process for the preparation of a new oxyhydrophenanthrene derivative.

Country Status (1)

Country Link
CH (1) CH254448A (en)

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