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CH254447A - Process for the preparation of a new oxyhydrophenanthrene derivative. - Google Patents

Process for the preparation of a new oxyhydrophenanthrene derivative.

Info

Publication number
CH254447A
CH254447A CH254447DA CH254447A CH 254447 A CH254447 A CH 254447A CH 254447D A CH254447D A CH 254447DA CH 254447 A CH254447 A CH 254447A
Authority
CH
Switzerland
Prior art keywords
sep
new
derivative
preparation
ethyl
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 CH254447A publication Critical patent/CH254447A/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 einen     1-Methylen-2-äIhyl-          7        -methoxy        -1,2,3;4-tetTahydro-phenanthren-2-          carbonsäuremethylester    zwecks     Überführung     der     Methylengruppierung    in einen     Methyl-          rest    mit hydrierenden Mitteln behandelt.  



  Für die     Überführung    der     1VIethylengrup-          pierung    in den     Methylrest    kann beispiels  weise die     katalytische    Hydrierung angewandt  werden.  



  Das neue Verfahrensprodukt, der     1-Me-          thyl    - 2     -@    äthyl - 7 -     methoxy-1,    2,     3,4-tetrahy        dro-          phenanthren-2-carbonsäuremethylester    vom       Sdp.        0101    mm 175 , soll therapeutische -Verwen  dung finden oder als Zwischenprodukt zur       Herstellung    therapeutisch verwendbarer Ver  bindungen dienen.  



       Beispiel:     1 Teil 1-     Methylen-    2 -     äthyl-        7-methoxy-          1,2,3,4    -     tetrahydro    -     phenanthren    - 2 -     carbon-          säuremethylester    der Formel  
EMI0001.0037     
    (erhalten z. B. aus dem analog dem Verfah  ren des Schweiz.

   Hauptpatentes     Nr.249115     erhältlichen 1-     Methyl    -1-     oxy    - 2-äthyl-7-me-         thoxy        -1,2,3,4-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     Moläquivalent     berechneten Menge Wasserstoff     wird    die  Lösung vom Katalysator     abfiltriert    und ein  gedampft. Durch     Destillation    des Rückstan  des im Hochvakuum erhält man den     1-Me-          tliyl    - 2 -     äthyl    - 7     -methoxy-1,2,3,4-tetrahydro-          phenanthren-2-carbonsäuremethylester    der  Formel  
EMI0001.0056     
    in Form     eines    farblosen Öls vom     Sdp.        0,01    mm  1.75 .  



  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-methylene-2-ethyl-7-methoxy-1,2,3; 4-tet-thahydro-phenanthrene-2-carboxylic acid methyl ester is used to convert the methylene group treated into a methyl residue with hydrogenating agents.



  Catalytic hydrogenation, for example, can be used to convert the 1VIethylene group into the methyl radical.



  The new process product, the 1-methyl-2 - @ ethyl-7-methoxy-1, 2, 3,4-tetrahydro- phenanthrene-2-carboxylic acid methyl ester with a bp. 0101 mm 175, should find therapeutic use or serve as an intermediate product for the preparation of therapeutically useful compounds.



       Example: 1 part 1 - methylene - 2 - ethyl - 7 - methoxy - 1,2,3,4 - tetrahydro - phenanthrene - 2 - carboxylic acid methyl ester of the formula
EMI0001.0037
    (obtained e.g. from the analogous procedure in Switzerland.

   Main patent No. 249115 available 1- methyl -1- oxy - 2-ethyl-7-methoxy -1,2,3,4-tetrahydro-phenanthrene-2-carboxylic acid methyl ester by elimination of water by means of formic acid or iodine in chloro form) 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. By distilling the residue in a high vacuum, 1-methyl-2-ethyl-7-methoxy-1,2,3,4-tetrahydrophenanthrene-2-carboxylic acid methyl ester of the formula is obtained
EMI0001.0056
    in the form of a colorless oil with a b.p. 0.01 mm 1.75.



  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-Methylen-2- äthyl - 7 - methoxy -1,2,3;4-tetrahydro -phen- anthren - 2 - carbonsäuremethylester zwecks Überführung der Methylengruppierung in einen Methylrest mit hydrierenden Mitteln behandelt. PATENT CLAIM: Process for the preparation of a new Oxyhydrophenanthren derivative, characterized in that a 1-methylene-2-ethyl-7-methoxy -1,2,3; 4-tetrahydro-phenanthrene-2-carboxylic acid methyl ester for the purpose of conversion Treated methylene grouping in a methyl radical with hydrogenating agents. Das neue Verfahrensprodukt, der 1-112e- thyl <B>-2)</B> - äthyl - 7 - methogy-1,2,3,4-tetrahydro- phenanthren-2 -carbonsäuremethylester vom Sdp. <B>0,01</B> mm 175 , soll therapeutische Verwen dung finden oder als Zwischenprodukt zur Herstellung therapeutisch verwendbarer Ver bindungen dienen. The new process product, the 1-112ethyl <B> -2) </B> - ethyl - 7 - methogy-1,2,3,4-tetrahydro- phenanthrene-2-carboxylic acid methyl ester with bp <B> 0, 01 </B> mm 175, should find therapeutic use or serve as an intermediate product for the production of therapeutically usable compounds. EMI0002.0014 ÜN@'E1@.91VS1'l@,trCl@@ <tb> 1. <SEP> Verfahren <SEP> gemäss <SEP> Patentanspruch, <SEP> da durch <SEP> gekennzeichnet, <SEP> dass <SEP> man <SEP> die <SEP> Hydrie rung <SEP> mittels <SEP> katalytisch <SEP> angeregtem <SEP> Was serstoff <SEP> vornimmt. <tb> 2. <SEP> Verfahren <SEP> gemäss <SEP> Patentanspruch, <SEP> da durch <SEP> gekennzeichnet, <SEP> dass <SEP> man <SEP> die <SEP> Hydrie rung <SEP> in <SEP> Eisessig <SEP> in <SEP> Gegenwart <SEP> von <SEP> Palla dium-Tierkohle <SEP> vornimmt. EMI0002.0014 ÜN @ 'E1 @ .91VS1'l @, trCl @@ <tb> 1. <SEP> method <SEP> according to <SEP> patent claim, <SEP> because it is characterized by <SEP>, <SEP> that <SEP> you <SEP> the <SEP> hydrogenation <SEP> using < SEP> catalytically <SEP> excited <SEP> hydrogen <SEP>. <tb> 2. <SEP> method <SEP> according to <SEP> patent claim, <SEP> as marked by <SEP>, <SEP> that <SEP> one <SEP> the <SEP> hydration <SEP> in < SEP> glacial acetic acid <SEP> in <SEP> presence <SEP> of <SEP> palladium animal charcoal <SEP>.
CH254447D 1944-01-10 1944-01-10 Process for the preparation of a new oxyhydrophenanthrene derivative. CH254447A (en)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
CH242609T 1944-01-10
CH254447T 1944-01-10

Publications (1)

Publication Number Publication Date
CH254447A true CH254447A (en) 1948-04-30

Family

ID=25728715

Family Applications (1)

Application Number Title Priority Date Filing Date
CH254447D CH254447A (en) 1944-01-10 1944-01-10 Process for the preparation of a new oxyhydrophenanthrene derivative.

Country Status (1)

Country Link
CH (1) CH254447A (en)

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