CH254449A - Process for the preparation of a new oxyhydrophenanthrene derivative. - Google Patents
Process for the preparation of a new oxyhydrophenanthrene derivative.Info
- Publication number
- CH254449A CH254449A CH254449DA CH254449A CH 254449 A CH254449 A CH 254449A CH 254449D A CH254449D A CH 254449DA CH 254449 A CH254449 A CH 254449A
- Authority
- CH
- Switzerland
- Prior art keywords
- new
- oxyhydrophenanthrene
- derivative
- preparation
- tetrahydro
- Prior art date
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-oxy-1,2,3,4-tetrahydro-phenanthren- 2-carbonsäuremethylester zwecks Überfüh- rung der Äthylidengruppierung in einen Äthylrest mit hydrierenden Mitteln behan delt.
Für die Überführung der Äthylidengrup- pierung in den Äthylrest kann beispielsweise die katalytische Hydrierung angewandt wer den.
Das neue Verfahrensprodukt, der 1-Äthyl- 2 -methyl - 7-oxy-,1,2,3,4-tetrahydro-phen- anthren-2-carbonsäuremethylestervom.F.117 soll therapeutische Verwendung finden oder als Zwischenprodukt zur Herstellung thera peutisch verwendbarer Verbindungen dienen.
Beispiel: 1 Teil 1-Äthyliden-2-methyl-7-oxy-1,2, 3,4 - tetrahydro - phenanthren - 2 - carb onsäure- methyles.ter vom F. 209 bis 211 der Formel
EMI0001.0032
(erhalten z.
B. aus dem nach dem Verfahren gemäss dem @schweiz. Hauptpatent Nr. 249115 erhältlichen 1- Äthyl-l-oxy-2-methyl-7-me- thoxy-1,2,3,4 -tetrahydro-phenanthren-2-car- bonsäuremethylester vom F. 153 durch Was serabspaltung mittels Ameisensäure oder Jod in Chloroform und anschliessender Spaltung der 7-Methoxy-Gruppe durch Erhitzen mit Pyridinhydrochlorid) wird in 30 Teilen Al kohol in Gegenwart von Platinoxyd unter Wasserstoff geschüttelt.
Nach Aufnahme der für 1 Moläquivalent berechneten Menge Was serstoff wird die Lösung vom Katalysator abfiltriert und eingedampft. Durch Umkri- stallisieren des Rückstandes aus verdünntem Methylalkohol erhält man den 1-Äthyl-2-me- thyl - 7-oxy-1,2,3,4-tetrahydro-phenanthren-2- carbonsäuremethylester der Formel
EMI0001.0052
in Form glänzender Blättchen vom F. 117 . 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-ethylidene-2-methyl-7-oxy-1,2,3,4-tetrahydro-phenanthrene-2-carboxylic acid methyl ester is used for the purpose of transferring the Ethylidene grouping in an ethyl radical treated 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-oxy-, 1,2,3,4-tetrahydro-phen-anthrene-2-carboxylic acid methyl ester from F.117 is intended to be used therapeutically or as an intermediate product for preparation usable connections.
Example: 1 part of 1-ethylidene-2-methyl-7-oxy-1,2,3,4 - tetrahydro - phenanthrene - 2 - carbonic acid methyles.ter of F. 209 to 211 of the formula
EMI0001.0032
(received e.g.
B. from the procedure according to @schweiz. Main patent no. 249115 available 1- ethyl-l-oxy-2-methyl-7-methoxy-1,2,3,4-tetrahydro-phenanthrene-2-carboxylic acid methyl ester from F. 153 by splitting off water with formic acid or Iodine in chloroform and subsequent cleavage of the 7-methoxy group by heating with pyridine hydrochloride) is shaken under hydrogen in 30 parts of alcohol in the presence of platinum oxide.
After taking up the amount of hydrogen calculated for 1 molar equivalent, the solution is filtered off from the catalyst and evaporated. By recrystallizing the residue from dilute methyl alcohol, 1-ethyl-2-methyl-7-oxy-1,2,3,4-tetrahydro-phenanthrene-2-carboxylic acid methyl ester of the formula is obtained
EMI0001.0052
in the form of shiny leaves from F. 117. The hydrogenation can also be carried out in glacial acetic acid in the presence of palladium animal charcoal.
Claims (1)
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
CH242609T | 1944-01-10 | ||
CH254449T | 1944-01-10 |
Publications (1)
Publication Number | Publication Date |
---|---|
CH254449A true CH254449A (en) | 1948-04-30 |
Family
ID=25728717
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
CH254449D CH254449A (en) | 1944-01-10 | 1944-01-10 | Process for the preparation of a new oxyhydrophenanthrene derivative. |
Country Status (1)
Country | Link |
---|---|
CH (1) | CH254449A (en) |
-
1944
- 1944-01-10 CH CH254449D patent/CH254449A/en unknown
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