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
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)
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) |
-
1944
- 1944-01-10 CH CH254450D patent/CH254450A/en unknown
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