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CH262162A - Process for the preparation of a new oxyhydrophenanthrene derivative. - Google Patents

Process for the preparation of a new oxyhydrophenanthrene derivative.

Info

Publication number
CH262162A
CH262162A CH262162DA CH262162A CH 262162 A CH262162 A CH 262162A CH 262162D A CH262162D A CH 262162DA CH 262162 A CH262162 A CH 262162A
Authority
CH
Switzerland
Prior art keywords
new
derivative
methoxy
carboxylic acid
tetrahydro
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 CH262162A publication Critical patent/CH262162A/en

Links

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-Methyliden-2-          methyl    - 7     -methoxy-1,2,3,4    -     tetrahy        dro    -     phen-          anthren    - 2 -     carbonsäure    -     methylester    zwecks  Überführung der     Methylidengruppierung    in  einen     Methylrest    mit hydrierenden Mitteln  behandelt.

      Für die Überführung der     Methylidengrup-          pierung    in den     Methylrest    kann beispielsweise  die katalytische Hydrierung dienen.  



  Das neue Verfahrensprodukt, der     1,2-Di-          methyl    - 7 -     methoxy-1,2,3,4    -     tetrahydro    -     phen-          anthren-2-carbonsäure-metliylester    vom F.104  bis 105 , soll therapeutische Verwendung fin  den oder als Zwischenprodukt zur Herstellung  therapeutisch verwendbarer Verbindungen  dienen.    <I>Beispiel:</I>    1 Teil 1-Methyliden-2-methyl-7-methoxy       1,2,3,4-tetrahydro-phenanthren-2-carbonsäure-          methylester    der Formel  
EMI0001.0026     
    (erhalten z.

   B. aus dem gemäss dein     schweiz.     Patent Nr. 257005 erhältlichen     1-Methyl-l-oxy-          2-methy        1-7-methoxy    -1,2,3,4     -tetrahydro    -     phen-          anthreri-2-carbonsäure-methylester    vom F.134    bis 136  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  1,2     -Dimethyl    -7     -methoxy-1,2,3,4        -tetrahydro-          phenanthren-2-carbonsäure-methylester    der  Formel  
EMI0001.0041     
    in Form derber Kristalle vom F. 104 bis 105 .  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-methylidene-2-methyl-7-methoxy-1,2,3,4-tetrahydro-phenanthrene-2-carboxylic acid treated methyl ester to convert the methylidene group into a methyl radical with hydrogenating agents.

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



  The new process product, the 1,2-dimethyl-7-methoxy-1,2,3,4-tetrahydro-phenanthrene-2-carboxylic acid methyl ester from F.104 to 105, is intended to be used in therapy or as Serve intermediate for the preparation of therapeutically useful compounds. <I> Example: </I> 1 part of 1-methylidene-2-methyl-7-methoxy 1,2,3,4-tetrahydro-phenanthrene-2-carboxylic acid methyl ester of the formula
EMI0001.0026
    (received e.g.

   B. from according to your Switzerland. Patent No. 257005 available 1-methyl-1-oxy-2-methy 1-7-methoxy -1,2,3,4-tetrahydro-phen-anthreri-2-carboxylic acid methyl ester from F.134 to 136 by dehydration means 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.

    By recrystallizing the residue from dilute methyl alcohol, the 1,2-dimethyl-7-methoxy-1,2,3,4-tetrahydrophenanthrene-2-carboxylic acid methyl ester of the formula is obtained
EMI0001.0041
    in the form of rough crystals from 104 to 105 mm. 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-Methyliden-2- methy 1- 7 - methoxy -1,2, 3,4 - tetrahydro - phen- anthren-2-carbonsäure-methylester zwecks Überführung der Methylldengruppierung in einen Methy lrest mit hydrierenden Mitteln behandelt. PATENT CLAIM: Process for the production of a new Oxyhydrophenanthren derivative, characterized in that one 1-methylidene-2- methy 1- 7-methoxy -1,2, 3,4 - tetrahydro - phenanthrene-2-carboxylic acid methyl ester treated with hydrogenating agents for the purpose of converting the methylene group into a methyl residue. Das neue Verfahrensprodukt, der 1,2-Di- methyl - 7 - methoxy -1,2, 3,4 - tetrahydro - phen- anthren-2-carbonsäure-methylester vom F.104 bis 105 , soll therapeutische Verwendung fin den oder als Zwischenprodukt zur Herstel lung therapeutisch verwendbarer Verbindun gen dienen. UNTERANSPRUCH; Verfahren gemäss Patentanspruch, da durch gekennzeichnet, dass man die Hydrie rung in Eisessig in Gegenwart von Palladium Tierkohle vornimmt. The new process product, the 1,2-dimethyl-7-methoxy-1,2,3,4-tetrahydro-phenanthrene-2-carboxylic acid methyl ester from F.104 to 105, is intended to be used in therapy or as Intermediate product for the production of therapeutically usable compounds. SUBCLAIM; Process according to patent claim, characterized in that the hydrogenation is carried out in glacial acetic acid in the presence of palladium charcoal.
CH262162D 1944-01-10 1944-01-10 Process for the preparation of a new oxyhydrophenanthrene derivative. CH262162A (en)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
CH262162T 1944-01-10
CH242609T 1944-01-10

Publications (1)

Publication Number Publication Date
CH262162A true CH262162A (en) 1949-06-15

Family

ID=25728721

Family Applications (1)

Application Number Title Priority Date Filing Date
CH262162D CH262162A (en) 1944-01-10 1944-01-10 Process for the preparation of a new oxyhydrophenanthrene derivative.

Country Status (1)

Country Link
CH (1) CH262162A (en)

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