CH355146A - Process for the preparation of N-alkyl-tetrahydroquinaldic acid amides - Google Patents
Process for the preparation of N-alkyl-tetrahydroquinaldic acid amidesInfo
- Publication number
- CH355146A CH355146A CH355146DA CH355146A CH 355146 A CH355146 A CH 355146A CH 355146D A CH355146D A CH 355146DA CH 355146 A CH355146 A CH 355146A
- Authority
- CH
- Switzerland
- Prior art keywords
- alkyl
- tetrahydroquinaldic
- acid
- preparation
- acid amides
- Prior art date
Links
- 150000001408 amides Chemical class 0.000 title claims description 7
- 238000000034 method Methods 0.000 title claims description 5
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 4
- OFBPSKIFXNJCAG-UHFFFAOYSA-N 1,2,3,4-tetrahydroquinoline-2-carboxamide Chemical compound C1=CC=C2NC(C(=O)N)CCC2=C1 OFBPSKIFXNJCAG-UHFFFAOYSA-N 0.000 claims description 2
- 239000002253 acid Substances 0.000 claims description 2
- 125000000217 alkyl group Chemical group 0.000 claims description 2
- 229910052757 nitrogen Inorganic materials 0.000 claims description 2
- ZEXKKIXCRDTKBF-UHFFFAOYSA-N quinoline-2-carboxamide Chemical compound C1=CC=CC2=NC(C(=O)N)=CC=C21 ZEXKKIXCRDTKBF-UHFFFAOYSA-N 0.000 claims description 2
- 150000003839 salts Chemical class 0.000 claims description 2
- UFFBMTHBGFGIHF-UHFFFAOYSA-N 2,6-dimethylaniline Chemical compound CC1=CC=CC(C)=C1N UFFBMTHBGFGIHF-UHFFFAOYSA-N 0.000 description 4
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 230000029936 alkylation Effects 0.000 description 3
- 238000005804 alkylation reaction Methods 0.000 description 3
- WFVMVMAUXYOQSW-UHFFFAOYSA-N quinoline-2-carbonyl chloride Chemical compound C1=CC=CC2=NC(C(=O)Cl)=CC=C21 WFVMVMAUXYOQSW-UHFFFAOYSA-N 0.000 description 3
- MLPVBIWIRCKMJV-UHFFFAOYSA-N 2-ethylaniline Chemical compound CCC1=CC=CC=C1N MLPVBIWIRCKMJV-UHFFFAOYSA-N 0.000 description 2
- MPPPKRYCTPRNTB-UHFFFAOYSA-N 1-bromobutane Chemical compound CCCCBr MPPPKRYCTPRNTB-UHFFFAOYSA-N 0.000 description 1
- WPEHSQMPKLFHTD-UHFFFAOYSA-N CN1C(CCC2CC=CC=C12)C(=O)O Chemical compound CN1C(CCC2CC=CC=C12)C(=O)O WPEHSQMPKLFHTD-UHFFFAOYSA-N 0.000 description 1
- CWNDGRZDAOKTCU-UHFFFAOYSA-N N-(2,6-dimethylphenyl)-1,2,3,4-tetrahydroquinoline-2-carboxamide Chemical compound CC1=CC=CC(C)=C1NC(=O)C1NC2=CC=CC=C2CC1 CWNDGRZDAOKTCU-UHFFFAOYSA-N 0.000 description 1
- -1 N-ethyl-tetrahydroquinaldic acid-2-ethylanilide Chemical compound 0.000 description 1
- 230000003444 anaesthetic effect Effects 0.000 description 1
- DENRZWYUOJLTMF-UHFFFAOYSA-N diethyl sulfate Chemical compound CCOS(=O)(=O)OCC DENRZWYUOJLTMF-UHFFFAOYSA-N 0.000 description 1
- 229940008406 diethyl sulfate Drugs 0.000 description 1
- VAYGXNSJCAHWJZ-UHFFFAOYSA-N dimethyl sulfate Chemical compound COS(=O)(=O)OC VAYGXNSJCAHWJZ-UHFFFAOYSA-N 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 230000002349 favourable effect Effects 0.000 description 1
- 238000005984 hydrogenation reaction Methods 0.000 description 1
- 239000003589 local anesthetic agent Substances 0.000 description 1
- 229960005015 local anesthetics Drugs 0.000 description 1
- KLHNXIPTNVCKOS-UHFFFAOYSA-N n-(2,6-dimethylphenyl)quinoline-2-carboxamide Chemical compound CC1=CC=CC(C)=C1NC(=O)C1=CC=C(C=CC=C2)C2=N1 KLHNXIPTNVCKOS-UHFFFAOYSA-N 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
- 229960004919 procaine Drugs 0.000 description 1
- MFDFERRIHVXMIY-UHFFFAOYSA-N procaine Chemical compound CCN(CC)CCOC(=O)C1=CC=C(N)C=C1 MFDFERRIHVXMIY-UHFFFAOYSA-N 0.000 description 1
- 230000001988 toxicity Effects 0.000 description 1
- 231100000419 toxicity Toxicity 0.000 description 1
Landscapes
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Description
Verfahren zur Herstellung von N-Alkyl-tetrahydrochinaldinsäureamiden Die vorliegende Erfindung bezieht sich auf ein Verfahren zur Herstellung von N-Alkyl-tetrahydro- chinaldinsäureamiden der Formel
EMI0001.0007
worin R eine Alkylgruppe und Ar einen 2-Alkyl- oder 2,6-Dialkyl-phenylrest bedeutet, das dadurch ge kennzeichnet ist,
dass man ein Chinaldinsäureamid der Formel
EMI0001.0013
hydriert und das erhaltene 1,2,3,4-Tetrahydrochinal- dinsäureamid am Ringstickstoff alkyliert.
Die so hergestellten Amide werden zweckmässig in ihre Säuresalze überführt.
Die neuen Amide haben sich als sehr gute Lokal anästhetika mit einer ebenfalls guten flächenanästhe- tischen Wirkung erwiesen. Der Effekt in bezug auf Toxizität ist vorteilhafter als derjenige von Prokain. <I>Beispiel 1</I> Durch Umsetzung von 191,5 Gewichtsteilen Chi- naldinsäurechlorid mit 121 Gewichtsteilen 2,6-Dime- thyl-anilin in 500 Gewichtsteilen trockenem Toluol,
zuerst bei Zimmertemperatur, danach eine Stunde bei 80 , erhält man in ungefähr quantitativer Ausbeute Chinaldinsäure-2,6-dimethylanilid. Beim Hydrieren in Essigsäure in Gegenwart von Platinoxyd bei einem Druck von 5 atü und bei einer Temperatur von 80 erhält man daraus Tetrahydrochinaldinsäure-2,6-di- methyl-anilid, das durch Alkylierung mit Dimethyl- sulfat in das N-Methyl-tetrahydrochinaldinsäure-2,
6- dimethyl-anilid überführt wird.
<I>Beispiel 2</I> Aus 191,5 Gewichtsteilen Chinaldinsäurechlorid und 121 Gewichtsteilen 2-Äthyl-anilin und Behand lung gemäss Beispiel 1 sowie anschliessende Alkyfe- rung mit Diäthylsulfat erhält man N-Äthyl-tetrahydro- chinaldinsäure-2-äthylanilid.
<I>Beispiel 3</I> Analog entsteht aus 191,5 Gewichtsteilen Chinal- dinsäurechlorid und 121 Gewichtsteilen 2,6-Dimethyl- anilin und Behandlung gemäss Beispiel 1 sowie an schliessende Alkylierwng mit n-Butyl-bromid N-n- Butyl-tetrahydrochinaldinsäure-2,6-dimethyl-anilid.
Process for the preparation of N-alkyl-tetrahydroquinaldic acid amides The present invention relates to a process for the preparation of N-alkyl-tetrahydroquinaldic acid amides of the formula
EMI0001.0007
where R is an alkyl group and Ar is a 2-alkyl or 2,6-dialkylphenyl radical, which is characterized
that you have a quinaldic acid amide of the formula
EMI0001.0013
hydrogenated and the resulting 1,2,3,4-tetrahydroquinaldic acid amide alkylated on the ring nitrogen.
The amides produced in this way are expediently converted into their acid salts.
The new amides have proven to be very good local anesthetics with an equally good surface anesthetic effect. The effect in terms of toxicity is more favorable than that of procaine. <I> Example 1 </I> By reacting 191.5 parts by weight of quinaldic acid chloride with 121 parts by weight of 2,6-dimethylaniline in 500 parts by weight of dry toluene,
first at room temperature, then for one hour at 80, quinaldic acid-2,6-dimethylanilide is obtained in approximately quantitative yield. Hydrogenation in acetic acid in the presence of platinum oxide at a pressure of 5 atmospheres and at a temperature of 80 gives tetrahydroquinaldic acid 2,6-dimethylanilide, which is converted into N-methyl-tetrahydroquinaldic acid by alkylation with dimethyl sulfate. 2,
6- dimethyl anilide is transferred.
<I> Example 2 </I> From 191.5 parts by weight of quinaldic acid chloride and 121 parts by weight of 2-ethyl-aniline and treatment according to Example 1 and subsequent alkylation with diethyl sulfate, N-ethyl-tetrahydroquinaldic acid-2-ethylanilide is obtained.
<I> Example 3 </I> Analogously, 191.5 parts by weight of quinaldic acid chloride and 121 parts by weight of 2,6-dimethylaniline and treatment according to Example 1 and subsequent alkylation with n-butyl bromide result in Nn-butyl-tetrahydroquinaldic acid- 2,6-dimethyl anilide.
Claims (1)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| SE355146X | 1956-01-18 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH355146A true CH355146A (en) | 1961-06-30 |
Family
ID=20308757
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH355146D CH355146A (en) | 1956-01-18 | 1956-12-29 | Process for the preparation of N-alkyl-tetrahydroquinaldic acid amides |
Country Status (1)
| Country | Link |
|---|---|
| CH (1) | CH355146A (en) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5521317A (en) * | 1993-10-22 | 1996-05-28 | American Cyanamid Co. | Processes for the preparation of pesticides and intermediates |
-
1956
- 1956-12-29 CH CH355146D patent/CH355146A/en unknown
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5521317A (en) * | 1993-10-22 | 1996-05-28 | American Cyanamid Co. | Processes for the preparation of pesticides and intermediates |
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