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
- 238000000034 method Methods 0.000 title claims description 8
- 238000002360 preparation method Methods 0.000 title description 3
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims description 4
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 3
- 229910052739 hydrogen Inorganic materials 0.000 claims description 3
- 239000001257 hydrogen Substances 0.000 claims description 3
- 238000005984 hydrogenation reaction Methods 0.000 claims description 3
- 229960000583 acetic acid Drugs 0.000 claims description 2
- 239000003610 charcoal Substances 0.000 claims description 2
- 239000003795 chemical substances by application Substances 0.000 claims description 2
- 150000001875 compounds Chemical class 0.000 claims description 2
- 239000012362 glacial acetic acid Substances 0.000 claims description 2
- 230000001225 therapeutic effect Effects 0.000 claims description 2
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 claims 2
- 238000006243 chemical reaction Methods 0.000 claims 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims 1
- 229910052763 palladium Inorganic materials 0.000 claims 1
- -1 1-ethylidene-2-methyl-7-propionyloxy-1,2,3, 4-tetrahydro- phenanthrene-2-carboxylic acid methyl ester Chemical compound 0.000 description 4
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
- XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 2
- QUPDWYMUPZLYJZ-UHFFFAOYSA-N ethyl Chemical compound C[CH2] QUPDWYMUPZLYJZ-UHFFFAOYSA-N 0.000 description 2
- 125000000219 ethylidene group Chemical group [H]C(=[*])C([H])([H])[H] 0.000 description 2
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 2
- AOJFQRQNPXYVLM-UHFFFAOYSA-N pyridin-1-ium;chloride Chemical compound [Cl-].C1=CC=[NH+]C=C1 AOJFQRQNPXYVLM-UHFFFAOYSA-N 0.000 description 2
- OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 description 1
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- 238000009903 catalytic hydrogenation reaction Methods 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- 230000032050 esterification Effects 0.000 description 1
- 238000005886 esterification reaction Methods 0.000 description 1
- 235000019253 formic acid Nutrition 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 239000011630 iodine Substances 0.000 description 1
- 229910052740 iodine Inorganic materials 0.000 description 1
- MUMZUERVLWJKNR-UHFFFAOYSA-N oxoplatinum Chemical compound [Pt]=O MUMZUERVLWJKNR-UHFFFAOYSA-N 0.000 description 1
- 229910003446 platinum oxide Inorganic materials 0.000 description 1
- 235000019260 propionic acid Nutrition 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- IUVKMZGDUIUOCP-BTNSXGMBSA-N quinbolone Chemical compound O([C@H]1CC[C@H]2[C@H]3[C@@H]([C@]4(C=CC(=O)C=C4CC3)C)CC[C@@]21C)C1=CCCC1 IUVKMZGDUIUOCP-BTNSXGMBSA-N 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
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 |
|---|---|---|---|
| CH254451T | 1944-01-10 | ||
| CH242609T | 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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