CH254446A - Process for the preparation of a new oxyhydrophenanthrene derivative. - Google Patents

Process for the preparation of a new oxyhydrophenanthrene derivative.

Info

Publication number
CH254446A
CH254446A CH254446DA CH254446A CH 254446 A CH254446 A CH 254446A CH 254446D A CH254446D A CH 254446DA CH 254446 A CH254446 A CH 254446A
Authority
CH
Switzerland
Prior art keywords
new
derivative
preparation
phenanthrene
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 CH254446A publication Critical patent/CH254446A/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

  

      Zusatzpatent    zum Hauptpatent Nr. 242609.    Verfahren zur Herstellung eines neuen     Oxyhydrophenanthren-Derivates.       Es wurde gefunden, dass man zu einem  neuen     Oxyhydrophenanthren-D:erivat    gelan  gen kann, wenn man einen     1-Äthyliden-2-          methyl    - 7     -methoxy        -1,2,3,4        -tetrahydro-phen-          anthren-2-carbonsäure-methylester    zwecks       Cberführung    der     Äthylidengruppierung    in  einen     Äthylrest    mit hydrierenden     Mitteln     behandelt.  



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



  Das neue Verfahrensprodukt, der     1-Athyl-          \?-methyl    - 7 -     methoxy-1,2,3,4-tetTahydro-phen-          anthren-2-carbonsäure-methylester    vom F. 76  bis 780, soll therapeutische Verwendung fin  den oder als     Zwischenprodukt    zur Herstel  lung therapeutisch     verwendbarer    Verbindun  gen dienen.  



       Beispiel:     1 Teil     1-Äthyliden-2.-methyl-7-methoxy-          1,2,8,4        -,        tetrahydro    -     phenanthren    - 2 -     carbom-          säure-methylester    vom F. 184     bis    1370 der       Formel     
EMI0001.0033     
    (erhalten z. B. aus dem     nach    dem Verfahren  gemäss dem Schweiz.

   Hauptpatent Nr. 249115  erhältlichen 1- Äthyl     -1-oxy-2-methyl-7-me-          thoxy    -1,2,8,4 - tetrahydro-phenanthren-2-ear-         bonsäure-methylester    vom F. 158  durch       Waseerabspaltung    mittels Ameisensäure oder     3.5     Jod in Chloroform)

   wird in 30 Teilen Alko  hol in Gegenwart von Platinoxyd unter Was  serstoff     geschüttelt.    Nach Aufnahme der für  1     Moläquivalent    berechneten Menge Wasser  stoff wird die Lösung vom Katalysator ab- 40  filtriert und     eingedampft.    Durch     Umkristal-          linieren    des Rückstandes aus verdünntem Me  thylalkohol erhält man den     1-Athyl-2-methyl-          7        -methoxy-1,2,3,4-tetrahydro-phenanthren-2-          carbonsäure-methylester    der Formel     45     
EMI0001.0050     
    in Form derber     :Kristalle    vom F. 76 bis 780.:

    Die Hydrierung kann auch in Eisessig in  Gegenwart von     Palladium-Tierkohle    vorge  nommen werden.



      Additional patent to main patent no. 242609. Process for the production of a new oxyhydrophenanthrene derivative. It has been found that a new oxyhydrophenanthrene-D: derivative can be obtained if a 1-ethylidene-2-methyl-7-methoxy-1,2,3,4-tetrahydro-phenanthrene-2-carboxylic acid is used -Methyl ester treated with hydrogenating agents for the purpose of converting the ethylidene group into an ethyl radical.



  Catalytic hydrogenation, for example, can be used to convert the ethylidene grouping into the ethyl radical.



  The new process product, the 1-ethyl- \? - methyl-7-methoxy-1,2,3,4-tetTahydro-phen-anthrene-2-carboxylic acid methyl ester from F. 76 to 780, is to be used in therapy or serve as an intermediate product for the produc- tion of therapeutically usable compounds.



       Example: 1 part of 1-ethylidene-2.-methyl-7-methoxy-1,2,8,4 -, tetrahydro - phenanthrene - 2 - carbomic acid methyl ester of mp 184 to 1370 of the formula
EMI0001.0033
    (obtained e.g. from the procedure according to Switzerland.

   Main patent no. 249115 obtainable 1-ethyl -1-oxy-2-methyl-7-methoxy -1,2,8,4-tetrahydro-phenanthrene-2-earboxylic acid methyl ester from F. 158 by elimination of water by means of formic acid or 3.5 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. The 1-ethyl-2-methyl-7-methoxy-1,2,3,4-tetrahydro-phenanthrene-2-carboxylic acid methyl ester of the formula 45 is obtained by recrystallizing the residue from dilute methyl alcohol
EMI0001.0050
    in the form of rough: crystals from F. 76 to 780 .:

    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-Äthyliden-2- methyl - 7 -methoxy @-1,2,3,4-tetrahydro-phen- anthren - 2 - earbonsäure-methylester zwecks Überführung der Äthylidengruppierung in einen Äthylrest mit hydrierenden Mitteln behandelt, DasIneue Verfahrensprodukt, der 1-Äthyl 2-methyl-7-methogy-1,2,3, PATENT CLAIM: Process for the production of a new Oxyhydrophenanthren derivative, characterized in that a 1-ethylidene-2-methyl-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 residue, the new product, 1-ethyl 2-methyl-7-methogy-1,2,3, 4-tetrahydro-phen- anthren-2-carbonsäure-methylester vom F. 76 bis 78 , soll therapeutische Verwendung fin den oder als Zwischenprodukt zur Herstel lung therapeutisch verwendbarer Verbindun gen: dienen. UNTERANSPRüCHE 1. Verfähren gemäss Patentanspruch, da durch gekennzeichnet, dass man die Hydrie- i xung mittels katalytisch angeregtem Wasser stoff vornimmt. 2. 4-tetrahydro-phenanthrene-2-carboxylic acid methyl ester with a melting point of 76 to 78, is intended to be used in therapy or as an intermediate for the preparation of therapeutically usable compounds. SUBClaims 1. Method according to patent claim, characterized in that the hydrogenation is carried out by means of catalytically activated hydrogen. 2. Verfahren gemäss Patentanspruch, da durch gekennzeichnet, dass man die Hydrie rung in Eisessig in Gegenwart von Palla- :i dium-Tierkohle vornimmt. Process according to patent claim, characterized in that the hydrogenation is carried out in glacial acetic acid in the presence of palladium animal charcoal.
CH254446D 1944-01-10 1944-01-10 Process for the preparation of a new oxyhydrophenanthrene derivative. CH254446A (en)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
CH254446T 1944-01-10
CH242609T 1944-01-10

Publications (1)

Publication Number Publication Date
CH254446A true CH254446A (en) 1948-04-30

Family

ID=25728714

Family Applications (1)

Application Number Title Priority Date Filing Date
CH254446D CH254446A (en) 1944-01-10 1944-01-10 Process for the preparation of a new oxyhydrophenanthrene derivative.

Country Status (1)

Country Link
CH (1) CH254446A (en)

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE1049855B (en) * 1959-02-05 CIBA Aktiengesellschaft, Base' (Schweiz) Process for the preparation of methylenehydrophenanthrenes

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE1049855B (en) * 1959-02-05 CIBA Aktiengesellschaft, Base' (Schweiz) Process for the preparation of methylenehydrophenanthrenes

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