CH254450A - Process for the preparation of a new oxyhydrophenanthrene derivative. - Google Patents

Process for the preparation of a new oxyhydrophenanthrene derivative.

Info

Publication number
CH254450A
CH254450A CH254450DA CH254450A CH 254450 A CH254450 A CH 254450A CH 254450D A CH254450D A CH 254450DA CH 254450 A CH254450 A CH 254450A
Authority
CH
Switzerland
Prior art keywords
new
derivative
preparation
carboxylic acid
acetoxy
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 CH254450A publication Critical patent/CH254450A/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-Äthyliden-2-          methyl    - 7 --     acetoxy    -1, 2,3,4 -     tetrahydro    -     phen-          anthren    - 2 -     carbonsäuremethylester    zwecks       Überführung    der     Athylidengruppierung    in  einen     Äthylrest    mit hydrierenden Mitteln  behandelt.  



  Für die Überführung der     Äthylidengrup-          pierung    in den     Äthylrest    kann beispielsweise  die katalytische Hydrierung angewandt wer  den.  



  Das neue     Verfahrensprodukt,    der     1-Athyl-          2    -     methyl    -     7-acetoxy-1,21,3,4-'tetrahydro-phen-          anthren-2-earbonsäure-methylester    vom     Sdp.          o.02        mm    180 , soll therapeutische     Verwendung     finden oder als     Zwischenprodukt    zur Herstel  lung therapeutisch verwendbarer Verbindun  gen dienen.  



       Beispiel:     1 Teil 1-     Athyliden    - 2 -     methyl-7-acetoxy-          1,2,3,4    -     tetrahydro    -     phenanthren    - 2 -     carbon-          säuremethylester    der Formel  
EMI0001.0037     
    (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;3"4-tetrahydro-phenanthren-2-car-         bonsäuremethylester    vom F. 153      durch     Wasserabspaltung mittels Ameisensäure oder  Jod in Chloroform, Spaltung der     7-Methoxy-          Gruppe    mit     Pyridinhydrochlorid    und an  schliessende     Veresterung    mit     Acetanhydrid     und     Pyridin)    wird in 30 Teilen Alkohol in  Gegenwart von Platinoxyd unter     Wasserstoff     geschüttelt.

   Nach Aufnahme der für 1     Mol-          ä.quivalent    berechneten     Menge    Wasserstoff  wird die Lösung vom Katalysator     abfiltriert     und     Jingedampft.        Dureh        Destillation    des  Rückstandes im     Hochvakuum    erhält man  den     1-Äthyl-2-mathyl-7-acetoxy-1,2,3,4-tetra-          hydro-phenanthren-2-,carbonsäuremethylester     der Formel  
EMI0001.0058     
    in Form eines farblosen Öls vom     Sdp.    0,02     m@     180 .  



  Die Hydrierung     kann    auch in Eisessig  in Gegenart von     Palladium-Tierkohle    vor  genommen 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-ethylidene-2-methyl-7-acetoxy-1, 2,3,4-tetrahydro-phenanthrene-2-carboxylic acid methyl ester is used Treated conversion of the Athylidengruppierung in an ethyl residue with hydrogenating agents.



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



  The new process product, the 1-ethyl-2-methyl-7-acetoxy-1,21,3,4-'tetrahydro-phen-anthrene-2-carboxylic acid methyl ester with a bp of 02 mm 180, is to be used in therapy or serve as an intermediate product for the production of therapeutically usable compounds.



       Example: 1 part 1-ethylidene - 2 - methyl-7-acetoxy- 1,2,3,4 - tetrahydro - phenanthrene - 2 - carboxylic acid methyl ester of the formula
EMI0001.0037
    (obtained e.g. from the procedure according to Switzerland.

   Main patent no. 249115 available 1-ethyl-1-oxy-2-methyl-7-methoxy-1,2; 3 "4-tetrahydro-phenanthrene-2-carboxylic acid methyl ester of F. 153 by dehydration using formic acid or iodine in Chloroform, cleavage of the 7-methoxy group with pyridine hydrochloride and subsequent esterification with acetic anhydride and pyridine) is shaken in 30 parts of alcohol in the presence of platinum oxide under hydrogen.

   After the amount of hydrogen calculated for 1 mol equivalent has been taken up, the solution is filtered off from the catalyst and evaporated. Distillation of the residue in a high vacuum gives 1-ethyl-2-mathyl-7-acetoxy-1,2,3,4-tetrahydro-phenanthrene-2-carboxylic acid methyl ester of the formula
EMI0001.0058
    in the form of a colorless oil with a boiling point of 0.02 m @ 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 Ogyhydrophenanthren-Derivates, dadurch ge kennzeichnet, dass man einen 1-Athyliden-2- methyl- 7 -acetoxy-1,2,3,4-,tehahydro -phen- anthren - 2 - carbonsäuremethylester zwecks Überführung der Äthylidengruppäerung in einen Äthylrest mit hydrierenden Mitteln behandelt. PATENT CLAIM: Process for the preparation of a new Ogyhydrophenanthren derivative, characterized in that a 1-Athyliden-2-methyl- 7-acetoxy-1,2,3,4-, tehahydro-phenanthrene-2-carboxylic acid methyl ester for the purpose of conversion the Äthylidengruppäerung treated in an ethyl residue with hydrogenating agents. Das neue Verfahrensprodukt, der 1-Athyl- 2 - methyl - 7-acetoxy-1, 2, 3,44-tetrahydro-phen- anthren-2-carbonsäuremethylester vom Sdp. o.oa 18C , soll therapeutische- Verwendung finden oder als Zwischenprodukt zur Herstel lung therapeutisch verwendbarer Verbindun gen dienen. UNTERANSPRÜCHE: 1. The new process product, the 1-ethyl-2-methyl-7-acetoxy-1, 2, 3,44-tetrahydro-phen-anthrene-2-carboxylic acid methyl ester of bp. O.oa 18C, is to be used therapeutically or as an intermediate product for the production of therapeutically usable compounds. SUBCLAIMS: 1. Verfahren gemäss Patentanspruch, da durch gekennzeichnet,. dass man die Hydrie rung mittels 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. Method according to claim, characterized by. that the hydrogenation is carried out using 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.
CH254450D 1944-01-10 1944-01-10 Process for the preparation of a new oxyhydrophenanthrene derivative. CH254450A (en)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
CH242609T 1944-01-10
CH254450T 1944-01-10

Publications (1)

Publication Number Publication Date
CH254450A true CH254450A (en) 1948-04-30

Family

ID=25728718

Family Applications (1)

Application Number Title Priority Date Filing Date
CH254450D CH254450A (en) 1944-01-10 1944-01-10 Process for the preparation of a new oxyhydrophenanthrene derivative.

Country Status (1)

Country Link
CH (1) CH254450A (en)

Similar Documents

Publication Publication Date Title
CH254450A (en) Process for the preparation of a new oxyhydrophenanthrene derivative.
CH254452A (en) Process for the preparation of a new oxyhydrophenanthrene derivative.
CH250806A (en) Process for the preparation of a new oxyhydrophenanthrene derivative.
CH254446A (en) Process for the preparation of a new oxyhydrophenanthrene derivative.
CH254451A (en) Process for the preparation of a new oxyhydrophenanthrene derivative.
CH254449A (en) Process for the preparation of a new oxyhydrophenanthrene derivative.
CH254447A (en) Process for the preparation of a new oxyhydrophenanthrene derivative.
CH262164A (en) Process for the preparation of a new oxyhydrophenanthrene derivative.
CH254448A (en) Process for the preparation of a new oxyhydrophenanthrene derivative.
CH262162A (en) Process for the preparation of a new oxyhydrophenanthrene derivative.
CH262163A (en) Process for the preparation of a new oxyhydrophenanthrene derivative.
CH248378A (en) Process for the preparation of a new oxyhydrophenanthrene derivative.
CH258190A (en) Process for the preparation of a new oxyhydrophenanthrene derivative.
DE493482C (en) Process for the preparation of p-menthol-3
CH258173A (en) Process for the preparation of a new oxyhydrophenanthrene derivative.
CH244982A (en) Process for the production of a lactone.
AT147319B (en) Process for the preparation of acyl derivatives of the octahydrofollicle hormones.
AT215420B (en) Process for the preparation of 1-methyl-3-pyrrolidyl-methyl alcohol
CH263483A (en) Process for the preparation of a new oxyhydrophenanthrene derivative.
CH258187A (en) Process for the preparation of a new oxyhydrophenanthrene derivative.
CH242609A (en) Process for the preparation of a new oxyhydrophenanthrene derivative.
CH245880A (en) Process for the preparation of a new oxyhydrophenanthrene derivative.
DE1290124B (en) Process for the preparation of lactones of saturated aliphatic delta-hydroxymono- or -dicarboxylic acids with 6 to 20 carbon atoms
CH245275A (en) Process for the preparation of a new compound of the cyclopentanopolyhydrophenanthrene series.
CH245879A (en) Process for the preparation of a new oxyhydrophenanthrene derivative.