CH270986A - Process for the preparation of the 4-amino-2-oxy-benzoic acid ester of a basic alcohol. - Google Patents
Process for the preparation of the 4-amino-2-oxy-benzoic acid ester of a basic alcohol.Info
- Publication number
- CH270986A CH270986A CH270986DA CH270986A CH 270986 A CH270986 A CH 270986A CH 270986D A CH270986D A CH 270986DA CH 270986 A CH270986 A CH 270986A
- Authority
- CH
- Switzerland
- Prior art keywords
- amino
- oxy
- benzoic acid
- preparation
- acid ester
- Prior art date
Links
- 239000005711 Benzoic acid Substances 0.000 title claims description 11
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 title claims description 8
- 238000000034 method Methods 0.000 title claims description 4
- 238000002360 preparation method Methods 0.000 title claims description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 4
- 239000002253 acid Substances 0.000 claims description 3
- 150000007513 acids Chemical class 0.000 claims description 3
- 239000002184 metal Substances 0.000 claims description 3
- 150000003839 salts Chemical class 0.000 claims description 3
- 238000000354 decomposition reaction Methods 0.000 claims description 2
- 238000002844 melting Methods 0.000 claims description 2
- 230000008018 melting Effects 0.000 claims description 2
- 239000000843 powder Substances 0.000 claims description 2
- 125000004185 ester group Chemical group 0.000 claims 1
- 235000019441 ethanol Nutrition 0.000 description 5
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 4
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 2
- 150000001414 amino alcohols Chemical class 0.000 description 2
- WPYMKLBDIGXBTP-UHFFFAOYSA-N Benzoic acid Natural products OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 1
- MZVQCMJNVPIDEA-UHFFFAOYSA-N [CH2]CN(CC)CC Chemical group [CH2]CN(CC)CC MZVQCMJNVPIDEA-UHFFFAOYSA-N 0.000 description 1
- 229910021529 ammonia Inorganic materials 0.000 description 1
- 235000010233 benzoic acid Nutrition 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 125000004494 ethyl ester group Chemical group 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 239000003589 local anesthetic agent Substances 0.000 description 1
- 229960005015 local anesthetics Drugs 0.000 description 1
- OKKJLVBELUTLKV-UHFFFAOYSA-N methanol Natural products OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 230000001225 therapeutic effect Effects 0.000 description 1
- 238000005809 transesterification reaction Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C231/00—Preparation of carboxylic acid amides
- C07C231/02—Preparation of carboxylic acid amides from carboxylic acids or from esters, anhydrides, or halides thereof by reaction with ammonia or amines
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C231/00—Preparation of carboxylic acid amides
- C07C231/12—Preparation of carboxylic acid amides by reactions not involving the formation of carboxamide groups
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Description
Verfahren zur Darstellung des 4-Amino-2-oxy-benzoesäureesters eines basischen Alkohols. Es wurde gefunden, dass die 4-Am.ino- 2-oxy-benzoesäure beim Verestern mit Amino- alkoholen Verbindungen ergibt, die zum Teil ausgezeichnete Lokalanästhetica darstellen.
Verbindungen dieser Art sind bisher nicht bekannt geworden. Sie können hergestellt werden durch Umesterung z. B. durch Erhitzen von 4-Amino-2-oxy-benzoesäure- methyl- oder -äthylestern mit einem Amino- alkohol, wobei Methyl- bzw. Äthylalkohol ab gespalten wird, oder aber durch Einwirkung eines Halogenalkylamins auf 4-Amino-2-oxy- benzoesäure oder ein Metallsalz derselben. Die Ester sind gewöhnlich dicke Flüssigkeiten, leicht löslich in Säuren.
Gegenstand des vorliegenden Patentes ist. ein Verfahren zur Herstellung des 4-Amino- 2-oxy-benzoesäureesters eines basischen Al kohols, welches dadurch gekennzeichnet ist, dass man 4-Amino-2-oxy-benzoesäure oder ein Metallsalz derselben mit einem ss-Halogen- äthyl-diäthylamin behandelt.
<I>Beispiel:</I> 22 Teile 4-Amino-2-oxy-benzoesäure wer den in 50 Teilen abs. Alkohol suspendiert lind mit 20 Teilen ss-Chlor-äthyl-@diäthylamin ver setzt und darauf unter Rüekfluss eine Stunde gekocht. Der Alkohol wird unter Vakuum abdestilliert, der Rückstand in Wasser gelöst und die entstandene Base durch Zusatz von Ammoniak ausgefällt und in Äther aufge nommen.
Die ätherische Lösung wird mit Wasser gewaschen, getrocknet und der Äther abdestilliert. Der Rückstand besteht aus 4- Amino - 2 , oxy - benzoesäure- diäthylamino- äthylester und stellt ein gelbliches Öl dar, leicht löslich in verdünnten Säuren. Das reine Monochlorhydrat des 4-Amino-2-oxy -benzoe- säure-,diäthy lamino-äthylesters ist ein weisses, in Wasser leicht lösliches Pulver vom F. 208 bis 210 (Zers.).
Das Monochlorhydrat des Endstoffes soll für therapeutische Zwecke verwendet werden.
Process for the preparation of the 4-amino-2-oxy-benzoic acid ester of a basic alcohol. It has been found that 4-amino-2-oxy-benzoic acid, when esterified with amino alcohols, gives compounds which, in some cases, are excellent local anesthetics.
Connections of this kind have not yet become known. They can be prepared by transesterification e.g. B. by heating 4-amino-2-oxy-benzoic acid methyl or ethyl esters with an amino alcohol, with methyl or ethyl alcohol being split off, or by the action of a haloalkylamine on 4-amino-2-oxy - benzoic acid or a metal salt thereof. The esters are usually thick liquids, easily soluble in acids.
The subject of the present patent is. a process for the preparation of the 4-amino-2-oxy-benzoic acid ester of a basic alcohol, which is characterized in that 4-amino-2-oxy-benzoic acid or a metal salt thereof is treated with an β-haloethyl-diethylamine.
<I> Example: </I> 22 parts of 4-amino-2-oxy-benzoic acid who are abs in 50 parts. Alcohol suspended with 20 parts of ss-chloro-äthyl- @ diethylamine ver sets and then boiled under reflux for one hour. The alcohol is distilled off under vacuum, the residue is dissolved in water and the base formed is precipitated by adding ammonia and taken up in ether.
The ethereal solution is washed with water, dried and the ether is distilled off. The residue consists of 4-amino-2, oxy-benzoic acid diethylamino-ethyl ester and is a yellowish oil, easily soluble in dilute acids. The pure monochlorohydrate of 4-amino-2-oxy-benzoic acid-, diethylamino-ethyl ester is a white powder, easily soluble in water, with a melting point of 208 to 210 (decomposition).
The monochlorohydrate of the end product should be used for therapeutic purposes.
Claims (1)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH270986T | 1948-05-24 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH270986A true CH270986A (en) | 1950-09-30 |
Family
ID=4478002
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH270986D CH270986A (en) | 1948-05-24 | 1948-05-24 | Process for the preparation of the 4-amino-2-oxy-benzoic acid ester of a basic alcohol. |
Country Status (1)
| Country | Link |
|---|---|
| CH (1) | CH270986A (en) |
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE943110C (en) * | 1950-08-01 | 1956-05-09 | Rheinpreussen Aktiengesellschf | Process for the preparation of esters of oxyaminobenzoic acids with amino alcohols substituted on the nitrogen atom |
| DE954424C (en) * | 1951-08-17 | 1956-12-20 | Rheinpreussen Ag | Process for the preparation of alkylaminoalkyl esters of aminooxybenzoic acids |
| US2780576A (en) * | 1951-12-24 | 1957-02-05 | Rheinpreussen Ag | Anaesthetic mixture |
-
1948
- 1948-05-24 CH CH270986D patent/CH270986A/en unknown
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE943110C (en) * | 1950-08-01 | 1956-05-09 | Rheinpreussen Aktiengesellschf | Process for the preparation of esters of oxyaminobenzoic acids with amino alcohols substituted on the nitrogen atom |
| DE954424C (en) * | 1951-08-17 | 1956-12-20 | Rheinpreussen Ag | Process for the preparation of alkylaminoalkyl esters of aminooxybenzoic acids |
| US2780576A (en) * | 1951-12-24 | 1957-02-05 | Rheinpreussen Ag | Anaesthetic mixture |
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