CH273077A - Process for the preparation of a new derivative of m-aminophenol. - Google Patents
Process for the preparation of a new derivative of m-aminophenol.Info
- Publication number
- CH273077A CH273077A CH273077DA CH273077A CH 273077 A CH273077 A CH 273077A CH 273077D A CH273077D A CH 273077DA CH 273077 A CH273077 A CH 273077A
- Authority
- CH
- Switzerland
- Prior art keywords
- butoxy
- nitro
- group
- benzyl
- amino
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims description 9
- 238000002360 preparation method Methods 0.000 title claims description 4
- CWLKGDAVCFYWJK-UHFFFAOYSA-N 3-aminophenol Chemical class NC1=CC=CC(O)=C1 CWLKGDAVCFYWJK-UHFFFAOYSA-N 0.000 title claims description 3
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 11
- -1 4-amino-2-n-butoxy-benzyl Chemical group 0.000 claims description 9
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 9
- 239000000155 melt Substances 0.000 claims description 6
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 4
- WVDDGKGOMKODPV-UHFFFAOYSA-N benzyl alcohol Substances OCC1=CC=CC=C1 WVDDGKGOMKODPV-UHFFFAOYSA-N 0.000 claims description 4
- 230000007062 hydrolysis Effects 0.000 claims description 4
- 238000006460 hydrolysis reaction Methods 0.000 claims description 4
- 239000003795 chemical substances by application Substances 0.000 claims description 3
- 238000000354 decomposition reaction Methods 0.000 claims description 3
- 230000003301 hydrolyzing effect Effects 0.000 claims description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 3
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 2
- 125000003277 amino group Chemical group 0.000 claims description 2
- 239000003638 chemical reducing agent Substances 0.000 claims description 2
- 150000001875 compounds Chemical class 0.000 claims description 2
- 229910052739 hydrogen Inorganic materials 0.000 claims description 2
- 239000001257 hydrogen Substances 0.000 claims description 2
- 239000013067 intermediate product Substances 0.000 claims description 2
- 239000000047 product Substances 0.000 claims description 2
- 125000001424 substituent group Chemical group 0.000 claims description 2
- 230000001419 dependent effect Effects 0.000 claims 2
- 239000007858 starting material Substances 0.000 claims 2
- 229940007550 benzyl acetate Drugs 0.000 claims 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims 1
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 6
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- JHJLBTNAGRQEKS-UHFFFAOYSA-M sodium bromide Chemical compound [Na+].[Br-] JHJLBTNAGRQEKS-UHFFFAOYSA-M 0.000 description 2
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
- CDAWCLOXVUBKRW-UHFFFAOYSA-N 2-aminophenol Chemical compound NC1=CC=CC=C1O CDAWCLOXVUBKRW-UHFFFAOYSA-N 0.000 description 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
- 239000007868 Raney catalyst Substances 0.000 description 1
- NPXOKRUENSOPAO-UHFFFAOYSA-N Raney nickel Chemical compound [Al].[Ni] NPXOKRUENSOPAO-UHFFFAOYSA-N 0.000 description 1
- 229910000564 Raney nickel Inorganic materials 0.000 description 1
- VMHLLURERBWHNL-UHFFFAOYSA-M Sodium acetate Chemical compound [Na+].CC([O-])=O VMHLLURERBWHNL-UHFFFAOYSA-M 0.000 description 1
- 229960000583 acetic acid Drugs 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- 239000000460 chlorine Substances 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 239000012362 glacial acetic acid Substances 0.000 description 1
- 125000005843 halogen group Chemical group 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 239000003208 petroleum Substances 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 239000001632 sodium acetate Substances 0.000 description 1
- 235000017281 sodium acetate Nutrition 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C213/00—Preparation of compounds containing amino and hydroxy, amino and etherified hydroxy or amino and esterified hydroxy groups bound to the same carbon skeleton
- C07C213/02—Preparation of compounds containing amino and hydroxy, amino and etherified hydroxy or amino and esterified hydroxy groups bound to the same carbon skeleton by reactions involving the formation of amino groups from compounds containing hydroxy groups or etherified or esterified hydroxy groups
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C215/00—Compounds containing amino and hydroxy groups bound to the same carbon skeleton
- C07C215/74—Compounds containing amino and hydroxy groups bound to the same carbon skeleton having hydroxy groups and amino groups bound to carbon atoms of six-membered aromatic rings of the same carbon skeleton
- C07C215/76—Compounds containing amino and hydroxy groups bound to the same carbon skeleton having hydroxy groups and amino groups bound to carbon atoms of six-membered aromatic rings of the same carbon skeleton of the same non-condensed six-membered aromatic ring
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Description
Verfahren zur Herstellung eines neuen Derivates des m-Amino-phenols. Gegenstand des Patentes ist ein Verfah ren zur Herstellung eines neuen Derivates des in .Amino-phenols, welches dadurch gekenn zeichnet ist, dass man eine Verbindung der Formel
EMI0001.0004
worin Z eine durch Reduktion in die Amino- gruppe überführbare Gruppe und X einen durch Hydrolyse durch die OB-Gruppe aus tauschbaren Substituenten, wie zum Beispiel ein Halogenatom, ein Aeyloxyrest usw., be deutet,
mit einem hydrolysierenden Mittel Und das Hy drolysenprodukt mit einem Re duktionsmittel behandelt. Der so erhaltene 4- Amino-2-n-butoxy-benzylalkohol schmilzt bei 60 bis<B>700</B> unscharf und löst sich leicht in Methanol und Äthanol. Er bildet ein Chlor hydrat, das bei 2500 unter Zersetzung schmilzt. Die neue Verbindung soll als Zwischenpro dukt Verwendung finden.
Beispiel <I>1:</I> 120 g 4-Nitro-2-n-butoxy-benzylbromid (F. 59 bis 600) werden mit<B>7G g</B> Natriumacetat und 1500 cm3 Eisessig 40 Stunden Rückfluss gekocht. Man trennt das entstandene Na- ti-iumbromid ab und dampft ein. Der Rück stand wird heiss mit Benzol ausgezogen, die Benzollösung verdampft und der Rückstand aus Ligroin (Kp.40 bis 650) umkristallisiert.
Ausbeute 65 g 4-Nitro-2-n-butoxy-benzylacetat vom Schmelzpunkt 60 bis 63o, das sind 59 0/0 der Theorie.
10 g 4-Nitro-2-n-butoxy-benzylacetat, 40 cm3 konzentrierter Salzsäure, 60 em3 Wasser und 120 em3 Alkohol werden 7 Stunden Rück fluss gekocht. Nach dem Abkühlen wird die ausgefallene feinkristalline Masse abgesaugt und aus 70 o/oigem Äthanol umkristallisiert. Man erhält 5,6 g 4-Nitro-2-n-butoxy-benzyl- alkoliol in Form farbloser Nadeln, die bei 85 bis<B>870</B> schmelzen.
30 g 4-Nitro-2-n-butoxy-benzylalkohol, ge löst in 400 cm3 abs. 1Vlethanol, werden mit 6 g Raney-Nickel unter einem Wasserstoffdruck von 1 at. 3 Stunden lang bei<B>190</B> geschüttelt.- Man befreit die Lösung vom Katalysator, engt im Vakuum ein und fällt den 4-Amino-2-n- butoxy-benzylalkohol aus Chloroform-Petrol- äther um.
Man erhält den neuen Alkohol so in 84 o/oiger Ausbeute als amorphes Pulver, das bei 60 bis<B>701)</B> urischarf schmilzt und sich leicht in Äthanol und Methanol löst. Das Chlorhydrat des Amins schmilzt bei 2500 unter Zersetzung.
<I>Beispiel</I> ,: 4-Nitro-2-n-butoxy-benzylbromidwird durch sechsstündiges Kochen mit einer Mischung von Dioxan/Wasser in den entsprechenden Alkohol übergeführt und dieser nach den An gaben im Beispiel 1 reduziert.
Process for the preparation of a new derivative of m-aminophenol. The subject of the patent is a process for the preparation of a new derivative of. Amino-phenol, which is characterized in that a compound of the formula
EMI0001.0004
where Z denotes a group which can be converted into the amino group by reduction and X denotes a substituent which can be exchanged by hydrolysis by the OB group, for example a halogen atom, an aeyloxy radical, etc.,
with a hydrolyzing agent and the hydrolysis product is treated with a reducing agent. The 4-amino-2-n-butoxy-benzyl alcohol thus obtained melts indistinctly at 60 to 700 and dissolves easily in methanol and ethanol. It forms a hydrate of chlorine, which melts at 2500 with decomposition. The new connection is to be used as an intermediate product.
Example <I> 1: </I> 120 g of 4-nitro-2-n-butoxy-benzyl bromide (F. 59 to 600) are refluxed with <B> 7G g </B> sodium acetate and 1500 cm3 of glacial acetic acid for 40 hours . The sodium bromide formed is separated off and evaporated. The residue is extracted hot with benzene, the benzene solution is evaporated and the residue is recrystallized from ligroin (bp 40 to 650).
Yield 65 g of 4-nitro-2-n-butoxy-benzyl acetate with a melting point of 60 to 63o, which is 59% of theory.
10 g of 4-nitro-2-n-butoxy-benzyl acetate, 40 cm3 of concentrated hydrochloric acid, 60 em3 of water and 120 em3 of alcohol are refluxed for 7 hours. After cooling, the precipitated finely crystalline mass is filtered off with suction and recrystallized from 70% ethanol. 5.6 g of 4-nitro-2-n-butoxy-benzylalkoliol are obtained in the form of colorless needles which melt at 85 to 870.
30 g of 4-nitro-2-n-butoxy-benzyl alcohol, dissolved in 400 cm3 of abs. 1Vlethanol, are shaken with 6 g of Raney nickel under a hydrogen pressure of 1 at. For 3 hours at <B> 190 </B>. The solution is freed from the catalyst, concentrated in vacuo and the 4-amino-2 is precipitated -n-butoxy-benzyl alcohol from chloroform-petroleum ether.
The new alcohol is thus obtained in 84% yield as an amorphous powder, which melts very sharply at 60 to 701) and dissolves easily in ethanol and methanol. The hydrochloride of the amine melts at 2500 with decomposition.
<I> Example </I>,: 4-Nitro-2-n-butoxy-benzyl bromide is converted into the corresponding alcohol by boiling for six hours with a mixture of dioxane / water and this alcohol is reduced according to the information in Example 1.
Claims (1)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH273077T | 1949-04-30 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH273077A true CH273077A (en) | 1951-01-31 |
Family
ID=4479076
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH273077D CH273077A (en) | 1949-04-30 | 1949-04-30 | Process for the preparation of a new derivative of m-aminophenol. |
Country Status (1)
| Country | Link |
|---|---|
| CH (1) | CH273077A (en) |
-
1949
- 1949-04-30 CH CH273077D patent/CH273077A/en unknown
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