CH254454A - Process for the preparation of a new oxyhydrophenanthrene carboxylic acid derivative. - Google Patents
Process for the preparation of a new oxyhydrophenanthrene carboxylic acid derivative.Info
- Publication number
- CH254454A CH254454A CH254454DA CH254454A CH 254454 A CH254454 A CH 254454A CH 254454D A CH254454D A CH 254454DA CH 254454 A CH254454 A CH 254454A
- Authority
- CH
- Switzerland
- Prior art keywords
- carboxylic acid
- preparation
- acid derivative
- new
- group
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims description 6
- 238000002360 preparation method Methods 0.000 title claims description 3
- 150000001732 carboxylic acid derivatives Chemical class 0.000 title description 2
- -1 carbomethoxy group Chemical group 0.000 claims description 9
- 150000001875 compounds Chemical class 0.000 claims description 3
- OCBFFGCSTGGPSQ-UHFFFAOYSA-N [CH2]CC Chemical compound [CH2]CC OCBFFGCSTGGPSQ-UHFFFAOYSA-N 0.000 claims description 2
- 239000002253 acid Substances 0.000 claims description 2
- 238000000354 decomposition reaction Methods 0.000 claims description 2
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 2
- 150000002902 organometallic compounds Chemical class 0.000 claims description 2
- 239000013067 intermediate product Substances 0.000 claims 1
- FRIJBUGBVQZNTB-UHFFFAOYSA-M magnesium;ethane;bromide Chemical compound [Mg+2].[Br-].[CH2-]C FRIJBUGBVQZNTB-UHFFFAOYSA-M 0.000 claims 1
- 238000004519 manufacturing process Methods 0.000 claims 1
- 239000000047 product Substances 0.000 claims 1
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- KBARGPSSEIXDQU-UHFFFAOYSA-N 3,4-dihydro-2h-phenanthren-1-one Chemical compound C1=CC2=CC=CC=C2C2=C1C(=O)CCC2 KBARGPSSEIXDQU-UHFFFAOYSA-N 0.000 description 1
- FLAKGKCBSLMHQU-UHFFFAOYSA-N CC[Mg] Chemical compound CC[Mg] FLAKGKCBSLMHQU-UHFFFAOYSA-N 0.000 description 1
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 1
- RDHPKYGYEGBMSE-UHFFFAOYSA-N bromoethane Chemical compound CCBr RDHPKYGYEGBMSE-UHFFFAOYSA-N 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-N hydrochloric acid Substances Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 1
- 230000003301 hydrolyzing effect Effects 0.000 description 1
- 229910052749 magnesium Inorganic materials 0.000 description 1
- 239000011777 magnesium Substances 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
- 238000010626 work up procedure Methods 0.000 description 1
- 229910052725 zinc Inorganic materials 0.000 description 1
- 239000011701 zinc Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C61/00—Compounds having carboxyl groups bound to carbon atoms of rings other than six-membered aromatic rings
- C07C61/16—Unsaturated compounds
- C07C61/39—Unsaturated compounds containing six-membered aromatic rings
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Description
Verfahren zur Herstellung eines neuen Oxyhydrophenanthrenearbonsäure-Derivates. Es wurde gefunden, dass man zu einem neuen Oxyhydrophenauthrencarbonsäure-De- rivat gelangen:
kann, wenn man in einem 1 Keto-1,2,3,4-tetrahydro-phenanthren, dass in 2-Stellulg neben einem n-P'ropylrest eine Carbomethoxygruppe und in 7-Stellung eine Methoxygruppe aufweist, die >C = 0-Gruppe in 1-,
Stellung durch Behandlung mit einer Äthylmetallverbindung und anschliessender Zersetzung der entstandenen Organometall- v erhindung mit hydrolysierenden Mitteln in die umwandelt.
EMI0001.0025
Zur Umwandlung der >C=D-Gruppe in 1-Stellung in die
EMI0001.0029
kann man den Ausgangsstoff beispielsweise mit einem Äthylmagnesium- oder -zink-halogenid oder einer Äthylalkaliverbindung umsetzen.
Das neue Verfahrensprodukt, der 1-Äthyl 1-oxy--2-n-propyl-7-methogy-1,2,3,4-tetra- hydro -phenanthren-2-carbonsäuremethylester vom F. 127 bis 128 , soll als Zwischenpro dukt zur Herstellung therapeutisch wertvol ler Verbindungen dienen.
<I>Beispiel:</I> Zu einer Grignard-Lösung, hergestellt aus 0,6 Gewichtsteilen Magnesium, 2 Volumen teilen Äthylbromid und 25 Volumenteilen Äther, lässt man in raschem Strahl 6,5 Ge wichtsteile 1- Keto - 2 - n-propyl-7-methoxy- 1,2,8,4 - tetrahydro - phenanthren - 2 - carbon- säure-methylester in 80 Volumenteilen Ben- zol zufliessen.
Man erwärmt noch eine halbe Stunde auf dem Wasserbad und zersetzt hierauf mit Eis-Salzsäure. Die übliche Auf arbeitung ergibt den 1-Äthyl-1-oxy-2-n-pro- pyl - 7 - methoxy =1,2,8.,4 - tetrahydro - phen- anthren-2-carbons:äure-methylester vomF.127 bis 128 .
Process for the preparation of a new oxyhydrophenanthrene carboxylic acid derivative. It was found that a new Oxyhydrophenauthrencarboxylic acid derivative can be obtained:
can, if one has in a 1-keto-1,2,3,4-tetrahydro-phenanthrene that in the 2-Stellulg in addition to an n-propyl radical a carbomethoxy group and in the 7-position a methoxy group which> C = 0- Group in 1-,
Positioned by treatment with an ethyl metal compound and subsequent decomposition of the resulting organometallic compound with hydrolysing agents into which converts.
EMI0001.0025
To convert the> C = D group in the 1-position into the
EMI0001.0029
you can implement the starting material for example with an ethylmagnesium or zinc halide or an ethylalkali compound.
The new process product, the 1-ethyl 1-oxy-2-n-propyl-7-methogy-1,2,3,4-tetra-hydro -phenanthrene-2-carboxylic acid methyl ester of F. 127 to 128, is said to be an intermediate pro used to produce therapeutically valuable compounds.
<I> Example: </I> To a Grignard solution, made from 0.6 parts by weight of magnesium, 2 parts by volume of ethyl bromide and 25 parts by volume of ether, 6.5 parts by weight of 1- keto - 2 - n- Propyl-7-methoxy-1,2,8,4-tetrahydro-phenanthrene-2-carboxylic acid methyl ester in 80 parts by volume of benzene.
The mixture is heated on the water bath for another half an hour and then decomposed with ice-hydrochloric acid. The usual work-up results in the 1-ethyl-1-oxy-2-n-propyl-7-methoxy = 1,2,8, 4-tetrahydro-phenanthrene-2-carboxylic acid methyl ester of F. 127 to 128.
Claims (1)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH249115T | 1944-01-10 | ||
| CH254454T | 1944-01-10 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH254454A true CH254454A (en) | 1948-04-30 |
Family
ID=25729331
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH254454D CH254454A (en) | 1944-01-10 | 1944-01-10 | Process for the preparation of a new oxyhydrophenanthrene carboxylic acid derivative. |
Country Status (1)
| Country | Link |
|---|---|
| CH (1) | CH254454A (en) |
-
1944
- 1944-01-10 CH CH254454D patent/CH254454A/en unknown
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