CH293013A - Process for the production of a new quinoline derivative. - Google Patents
Process for the production of a new quinoline derivative.Info
- Publication number
- CH293013A CH293013A CH293013DA CH293013A CH 293013 A CH293013 A CH 293013A CH 293013D A CH293013D A CH 293013DA CH 293013 A CH293013 A CH 293013A
- Authority
- CH
- Switzerland
- Prior art keywords
- amino
- parts
- quinoline derivative
- production
- water
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims description 5
- 125000002943 quinolinyl group Chemical class N1=C(C=CC2=CC=CC=C12)* 0.000 title claims 2
- 238000004519 manufacturing process Methods 0.000 title description 2
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 claims description 8
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 4
- 229910021529 ammonia Inorganic materials 0.000 claims description 4
- 238000000354 decomposition reaction Methods 0.000 claims description 4
- 238000002844 melting Methods 0.000 claims description 4
- 230000008018 melting Effects 0.000 claims description 4
- 239000000126 substance Substances 0.000 claims description 4
- 150000001450 anions Chemical class 0.000 claims description 2
- 150000001768 cations Chemical class 0.000 claims description 2
- 238000002360 preparation method Methods 0.000 claims description 2
- 150000003839 salts Chemical class 0.000 claims description 2
- 230000000654 trypanocidal effect Effects 0.000 claims description 2
- 125000000101 thioether group Chemical group 0.000 claims 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 8
- FVAUCKIRQBBSSJ-UHFFFAOYSA-M sodium iodide Chemical compound [Na+].[I-] FVAUCKIRQBBSSJ-UHFFFAOYSA-M 0.000 description 6
- 239000000203 mixture Substances 0.000 description 4
- 239000007787 solid Substances 0.000 description 4
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- 238000010438 heat treatment Methods 0.000 description 2
- 235000009518 sodium iodide Nutrition 0.000 description 2
- HJGREUUTQZOVTH-UHFFFAOYSA-N 4-methoxy-2-methylquinolin-6-amine Chemical compound C1=C(N)C=C2C(OC)=CC(C)=NC2=C1 HJGREUUTQZOVTH-UHFFFAOYSA-N 0.000 description 1
- 235000019270 ammonium chloride Nutrition 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 239000003610 charcoal Substances 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 239000003085 diluting agent Substances 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- DKAGJZJALZXOOV-UHFFFAOYSA-N hydrate;hydrochloride Chemical compound O.Cl DKAGJZJALZXOOV-UHFFFAOYSA-N 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 150000003248 quinolines Chemical class 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 150000003568 thioethers Chemical group 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
- C07D401/12—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings linked by a chain containing hetero atoms as chain links
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
Description
Verfahren zur Herstellung eines neuen Chinolinderivates. Wiegenstand der vorliegenden Erfindung ist, ein Verfahren zur Herstellung des 4-Amino- (' - C- amino - 6'- methyl - pyrimidyl -4'-amino) - < -hinaldin-1,1'-dimethjodids.
Erfindungsgemäss wird diese neue Verbin- dun,y dadurch erhalten, dass man Ammoniak mit einem Salz eines Kations der Formel
EMI0001.0015
in welcher X und Y Äther- oder Thioäther- rest.e bedeuten, umsetzt und hierauf eine das :Todanion liefernde Substanz zur I?.in-,#,irkung bringt.
Das Produkt ist eine blassgelbe, kristalline Substanz vom Schmelzpunkt 310 bis 315 C (unter Zersetzung) und besitzt trypanozide Wirkung.
Die Umsetzung mit dem Ammoniak wird zweekmässigerweise durch Erhitzen der Reak tionsteilnehmer in einem flüssigen Lösungs mittel oder Verdünnungsmittel durchgeführt. Das Erhitzen erfolgt mit Vorteil in einem geschlossenen Gefäss.
Im folgenden Beispiel bedeuten die Teile Gewichtsteile. <I>Beispiel:</I> 2 Teile 6-(2'-Methylthio-6'-methyl-pyrimi- dyl-4'-amino) -4-methoxy-chinaldin-1,1'-dimeth- jodid, 2 Teile Ammoniumchlorid und 20 Teile einer Lösung von Ammoniak in Äthanol (bei -- 50 C gesättigt) werden während 6 Stunden in einem geschlossenen Gefäss auf l40 C er hitzt. Hierauf kühlt man das Gefäss ab, ver mischt dessen Inhalt mit 300 Teilen Wasser und neutralisiert das -Gemisch mit Salzsäure. Dann filtriert man das Gemisch und löst den festen Rückstand in 100 Teilen siedendem Wasser. Die Lösung wird mit Kohle behandelt und filtriert.
Das Filtrat wird bei 70 bis 80 C mit 30prozentiger wässeriger Natriumjodid- lösung behandelt und filtriert. Der feste Rück stand besteht aus 4-Amino-6-(2'-amino-6'-me- thyl-pyrimidyl-4'-amino )-chinaldin-1,1'-dimeth- jodid vom Schmelzpunkt 312 bis 313 C (unter Zersetzung).
Das für das in diesem Beispiel beschrie bene Verfahren verwendete Ausgangsmaterial kann wie folgt erhalten werden: Heisse Lösungen von 4,4 Teilen 6-Amino-4 methoxy-chinaldin-methochlorid-hydrochl.orid- monohydrat in 100 Teilen Wasser und 4,75 Teilen 4-Chlor-2-methylthio-6-methyl-pyrimi- din-l-methjodid in 45 Teilen Wasser werden miteinander vermischt und während 1 Stunde unter Rückfluss sieden gelassen, worauf das Gemisch filtriert wird. Der feste Rückstand wird mit Wasser gewaschen und in 200 Tei len Wasser gelöst. Die Lösung wird mit einer hüsung von 6 Teilen Natriumjodid in 50 Teilen heissem Wasser versetzt.
Das Gemisch wird abgekühlt und filtriert und der feste Rückstand aus Wasser umkristallisiert. Man erhält 6-(2'--VTethylthio-6'-methyl-pyrimidyl-4'- amino) - 4-methoxy - chinaldin-1,1'-dimethjodid- inonohydrat vom Schmelzpunkt 213 C (unter Zersetzung).
Process for the production of a new quinoline derivative. The cradle of the present invention is a process for the preparation of 4-amino- ('- C-amino-6'-methyl-pyrimidyl -4'-amino) - <-hinaldine-1,1'-dimethiodide.
According to the invention, this new compound is obtained by mixing ammonia with a salt of a cation of the formula
EMI0001.0015
in which X and Y mean ether or thioether residues.e, converts and then brings about a substance that delivers the dead anion to the I? .in -, #, effect.
The product is a pale yellow, crystalline substance with a melting point of 310 to 315 C (with decomposition) and has a trypanocidal effect.
The reaction with the ammonia is carried out in two ways by heating the reactants in a liquid solvent or diluent. The heating is advantageously carried out in a closed vessel.
In the following example, the parts mean parts by weight. <I> Example: </I> 2 parts 6- (2'-methylthio-6'-methyl-pyrimidyl-4'-amino) -4-methoxy-quinaldine-1,1'-dimethiodide, 2 Parts of ammonium chloride and 20 parts of a solution of ammonia in ethanol (saturated at -50 ° C.) are heated to 140 ° C. in a closed vessel for 6 hours. The vessel is then cooled, its contents are mixed with 300 parts of water and the mixture is neutralized with hydrochloric acid. The mixture is then filtered and the solid residue is dissolved in 100 parts of boiling water. The solution is treated with charcoal and filtered.
The filtrate is treated at 70 to 80 C with 30 percent aqueous sodium iodide solution and filtered. The solid residue consists of 4-amino-6- (2'-amino-6'-methyl-pyrimidyl-4'-amino) -quinaldine-1,1'-dimethiodide with a melting point of 312 to 313 C ( with decomposition).
The starting material used for the process described in this example can be obtained as follows: Hot solutions of 4.4 parts of 6-amino-4-methoxy-quinaldine methochloride hydrochloride monohydrate in 100 parts of water and 4.75 parts of 4 -Chlor-2-methylthio-6-methyl-pyrimidine-1-methiodide in 45 parts of water are mixed together and allowed to reflux for 1 hour, after which the mixture is filtered. The solid residue is washed with water and dissolved in 200 parts of water. The solution is mixed with 6 parts of sodium iodide in 50 parts of hot water.
The mixture is cooled and filtered and the solid residue is recrystallized from water. 6- (2'-VTethylthio-6'-methyl-pyrimidyl-4'-amino) -4-methoxy-quinaldine-1,1'-dimethiodidynonohydrate with a melting point of 213 ° C. (with decomposition) is obtained.
Claims (1)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB293012X | 1948-11-05 | ||
| GB293013X | 1948-11-05 | ||
| CH287390T | 1949-11-05 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH293013A true CH293013A (en) | 1953-08-31 |
Family
ID=27178163
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH293013D CH293013A (en) | 1948-11-05 | 1949-11-05 | Process for the production of a new quinoline derivative. |
Country Status (1)
| Country | Link |
|---|---|
| CH (1) | CH293013A (en) |
-
1949
- 1949-11-05 CH CH293013D patent/CH293013A/en unknown
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