CH254451A - Process for the preparation of a new oxyhydrophenanthrene derivative. - Google Patents
Process for the preparation of a new oxyhydrophenanthrene derivative.Info
- Publication number
- CH254451A CH254451A CH254451DA CH254451A CH 254451 A CH254451 A CH 254451A CH 254451D A CH254451D A CH 254451DA CH 254451 A CH254451 A CH 254451A
- Authority
- CH
- Switzerland
- Prior art keywords
- new
- derivative
- methyl
- carboxylic acid
- phenanthrene
- 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)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Description
Verfahren zur Herstellung eines neuen Oxybydrophenanthren-Derivates.'- Es wurde gefunden, dass' man zu einem neue, Oxyhydrophenanthren -Derivat ge langen kann, wenn man einen 1-Äthyliden- 2 -methyl- 7-propionyloxy-1,2,3,4-tetrahydro- phenanthren-2-carbonsäuremethylesterzwecks Überführung der Äthylidengruppierung in einen Äthylrest mit hydrierenden Mitteln behandelt.
Für die Überführung der Äthylidengrup- pierung in den Athylrest kann beispielsweise die katalytische Hydrierung angewandt wer den. ' Das neue Verfahrensprodukt, der 1-Äthyl- 2 -mebhyl-7-propionyloxy-1,2,3,4-tetrahydro- phenanthren-2-carbonsäuremethylester vom F.
89 bis 90 , soll therapeutische Verwen dung finden oder als Zwischenprodukt zur Herstellung therapeutisch verwendbarer Ver bindungen dienen.
Beispiel: 1 Teil 1-Äthyliden-2-methyl-7-propionyl- oxy-1, 2, 3,4-tetrahydro-phenanthren-2-carbon- säuremethylester der Formel
EMI0001.0029
(erhalten z.
B. aus dem nach dem Verfahren gemäss dem echweiz. Hauptpatent Nr. 24911;7 erhältlichen 1- Äthyl -1- 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, Spaltung der 7-Methoxy- Gruppe durch Erhitzen mit Pyridinhydro- chlorid und anschliessende Veresterung mit Propionsäureamhydxid und Pyridin)
wird in. 30 Teilen Alkohol in Gegenwart von Platinoxyd unter Wasserstoff geschüttelt. Nach Auf nahme der für 1 Moläquivalent berechneten Menge Wasserstoff wird die Lösung vom Katalysator abfiltriert und eingedampft.
Durch Umkristallisieren des Rückstandes aus verdünntem Methylalkohol erhält man den 1- Äthyl - 2 - methyl-7-propionyl-oxy-1,2, 3,4- tetrahydro- phenanthren- 2- carbonsäure- methylester der Formel
EMI0001.0062
in Form farbloser Kristalle vom F. 89'bis 90 . Die Hydrierung kann auch in Eisessig in Gegenwart von ]#älladium-Tierkohle vorge nommen werden.
Process for the preparation of a new oxybydrophenanthrene derivative .'- It has been found that 'you can get to a new oxyhydrophenanthrene derivative if you have a 1-ethylidene-2-methyl-7-propionyloxy-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 radical.
Catalytic hydrogenation, for example, can be used to convert the ethylidene group into the ethyl radical. 'The new process product, the methyl 1-ethyl-2-methyl-7-propionyloxy-1,2,3,4-tetrahydrophenanthrene-2-carboxylate from F.
89 to 90, should find therapeutic use or serve as an intermediate for the preparation of therapeutically useful compounds.
Example: 1 part of 1-ethylidene-2-methyl-7-propionyl-oxy-1, 2, 3,4-tetrahydro-phenanthrene-2-carboxylic acid methyl ester of the formula
EMI0001.0029
(received e.g.
B. from the according to the procedure according to echweiz. Main patent no. 24911; 7 available 1- ethyl-1-oxy-2-methyl-7-methoxy-1,2,3,4-tetrahydro-phenanthrene-2-carboxylic acid methyl ester from F.
153 by splitting off water by means of formic acid or iodine in chloroform, splitting of the 7-methoxy group by heating with pyridine hydrochloride and subsequent esterification with propionic acid and pyridine)
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.
Recrystallization of the residue from dilute methyl alcohol gives 1-ethyl-2-methyl-7-propionyl-oxy-1,2,3,4-tetrahydrophenanthrene-2-carboxylic acid methyl ester of the formula
EMI0001.0062
in the form of colorless crystals from F. 89 'to 90. The hydrogenation can also be carried out in glacial acetic acid in the presence of äladium animal charcoal.
Claims (1)
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
CH242609T | 1944-01-10 | ||
CH254451T | 1944-01-10 |
Publications (1)
Publication Number | Publication Date |
---|---|
CH254451A true CH254451A (en) | 1948-04-30 |
Family
ID=25728719
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
CH254451D CH254451A (en) | 1944-01-10 | 1944-01-10 | Process for the preparation of a new oxyhydrophenanthrene derivative. |
Country Status (1)
Country | Link |
---|---|
CH (1) | CH254451A (en) |
-
1944
- 1944-01-10 CH CH254451D patent/CH254451A/en unknown
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