CH254448A - Process for the preparation of a new oxyhydrophenanthrene derivative. - Google Patents
Process for the preparation of a new oxyhydrophenanthrene derivative.Info
- Publication number
- CH254448A CH254448A CH254448DA CH254448A CH 254448 A CH254448 A CH 254448A CH 254448D A CH254448D A CH 254448DA CH 254448 A CH254448 A CH 254448A
- Authority
- CH
- Switzerland
- Prior art keywords
- new
- derivative
- preparation
- carboxylic acid
- propylidene
- 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-Propyliden-2- methyl- 7 -methoxy-1,2,3,4-tetrahydro-phen- anthren-2-carbonsäuremethylester zwecks Überführung der Propylidengruppierung in einen Propylrest mit hydrierenden Mitteln behandelt.
Für die Überführung der Propyliden- grüppierung in den Propylrest kann bei spielsweise die katalytische Hydrierung an gewandt werden.
Das neue Verfahrensprodukt, der 1-Pro- pyl-2#,methyl-7-methoxy-1,2,3,4 ;tetrahydro- phenanthren-2-carbonsäuremethylester vom Sdp. o,oz ", 180 , soll therapeutische Verwen dung finden oder als Zwischenprodukt zur Herstellung therapeutisch verwendbarer Ver bindungen dienen. Beispiel: 1 Teil 1-Propyliden-2-methyl-7-methoxy 1,2,3,4-tetrahydrophenanthren-2-carbonsäure- methylester der Formel
EMI0001.0025
(erhalten z.
B. aus dem analog dem Verfah ren des. schweiz. Hauptpatentes- Nr. 249115 erhältlichen 1- Propyl -1-oxy-2-methyl-7-me- thoxy H 1',2,3,41-'.tetrahydro-phenanthren.-2-car- bonsäuremethylester durch Wasserabspaltung mittels Ameisensäure oder Jod in Chloro form) wird in 30 Teilen Alkohol in Gegen wart von Platinoxyd unter Wasserstoff ge schüttelt.
Nach Aufnahme der für 1 Moläqui- valent berechneten Menge Wasserstoff wird die Lösung vom Katalysator abfiltriert und eingedampft.
Durch Destillation des R,ück- standes im Hochvakuum erhält man den 1-Propyl - 2 -methyl - 7-metJioxy-1,2,3,4-tetra- hydro-phenanthren-2-carbonsäure-methylester der Formel
EMI0001.0052
in Form eines farblosen Öls vom Sdp. o,oZ mm 180 . 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-propylidene-2-methyl-7-methoxy-1,2,3,4-tetrahydro-phenanthrene-2-carboxylic acid methyl ester is used for conversion treated the propylidene group in a propyl radical with hydrogenating agents.
Catalytic hydrogenation, for example, can be used to convert the propylidene grouping into the propyl radical.
The new product of the process, the 1-propyl-2 #, methyl-7-methoxy-1,2,3,4; tetrahydro- phenanthrene-2-carboxylic acid methyl ester of bp. O, oz ", 180, is to find therapeutic use or serve as an intermediate product for the preparation of therapeutically useful compounds Example: 1 part of 1-propylidene-2-methyl-7-methoxy 1,2,3,4-tetrahydrophenanthrene-2-carboxylic acid methyl ester of the formula
EMI0001.0025
(received e.g.
B. from the analogous to the procedural ren des. Switzerland. Main patent No. 249115 available 1-propyl -1-oxy-2-methyl-7-methoxy H 1 ', 2,3,41 -'. Tetrahydro-phenanthrene-2-carboxylic acid methyl ester by elimination of water with formic acid or Iodine in chloro form) is shaken under hydrogen in 30 parts of alcohol in the presence of platinum oxide.
After the amount of hydrogen calculated for 1 molar equivalent has been taken up, the solution is filtered off from the catalyst and evaporated.
Distilling the residue in a high vacuum gives the 1-propyl-2-methyl-7-methoxy-1,2,3,4-tetrahydrophenanthrene-2-carboxylic acid methyl ester of the formula
EMI0001.0052
in the form of a colorless oil of bp o, oZ mm 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 | ||
CH254448T | 1944-01-10 |
Publications (1)
Publication Number | Publication Date |
---|---|
CH254448A true CH254448A (en) | 1948-04-30 |
Family
ID=25728716
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
CH254448D CH254448A (en) | 1944-01-10 | 1944-01-10 | Process for the preparation of a new oxyhydrophenanthrene derivative. |
Country Status (1)
Country | Link |
---|---|
CH (1) | CH254448A (en) |
-
1944
- 1944-01-10 CH CH254448D patent/CH254448A/en unknown
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