DE828248C - Process for the preparation of new quaternary quinoline derivatives - Google Patents
Process for the preparation of new quaternary quinoline derivativesInfo
- Publication number
- DE828248C DE828248C DES17759A DES0017759A DE828248C DE 828248 C DE828248 C DE 828248C DE S17759 A DES17759 A DE S17759A DE S0017759 A DES0017759 A DE S0017759A DE 828248 C DE828248 C DE 828248C
- Authority
- DE
- Germany
- Prior art keywords
- radicals
- quinoline derivatives
- preparation
- maquenne
- block
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired
Links
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D215/00—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems
- C07D215/02—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom
- C07D215/16—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D215/20—Oxygen atoms
- C07D215/24—Oxygen atoms attached in position 8
- C07D215/26—Alcohols; Ethers thereof
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D215/00—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems
- C07D215/02—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom
- C07D215/16—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D215/20—Oxygen atoms
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Quinoline Compounds (AREA)
Description
Verfahren zur Herstellung von neuen quartären Chinolinderivaten Die vorliegende Erfindung betrifft die Herstellung von neuen Chinolinderivaten, deren Molekül von zwei substituierten Chinolinringen, die durch eine an den Kernstickstoffatomen desChinolins befindliche Kohlenwasserstoffkette verbunden sind, gebildet ist, wobei diese Derivate in Form von quartären Ammoniumsalzen vorliegen.Process for the preparation of new quaternary quinoline derivatives The present invention relates to the production of new quinoline derivatives, their Molecule of two substituted quinoline rings linked by one on the core nitrogen atoms desquinoline hydrocarbon chain are linked, is formed, wherein these derivatives are in the form of quaternary ammonium salts.
Diese Verbindungen werden durch die allgemeine Formel wiedergegeben, in der n eine ganze Zahl gleich oder größer als 2 bedeutet und die Alkylenkette gegebenenfalls verzweigt sein kann. Y sind Halogenatome oder Säurereste und R Hydroxyl- oder Alkylreste. - Die Reste R können auch untereinander verbunden sein und eine einzige Dioxyalkylenkettebilden.These compounds are represented by the general formula reproduced, in which n is an integer equal to or greater than 2 and the alkylene chain can optionally be branched. Y are halogen atoms or acid radicals and R are hydroxyl or alkyl radicals. The radicals R can also be linked to one another and form a single dioxyalkylene chain.
Es sei erwähnt, daß die Reste R sich an irgendeiner der freien Stellen der Chinolinringe und nicht nur in 8-Stellung befinden können.It should be noted that the radicals R are in any of the vacant positions of the quinoline rings and not just in the 8-position.
Gemäß der vorliegenden Erfindung erhält man diese Verbindungen, wenn man die durch die Reste R substituierten Chinoline mit freier Z-StelIung, die der obenerwähnten Formel entsprechen, mit einem dihalogenierten aliphatischen Kohlenwasserstoff umsetzt.According to the present invention, these compounds are obtained when one the quinolines substituted by the radicals R with free Z-StelIung, which the correspond to the formula mentioned above, with a dihalogenated aliphatic hydrocarbon implements.
Nötigenfalls kann man dann die so erhaltenen halogenierten Salze in Chinolinabkömmlinge mit anderen Säureresten durch allgemein bekannte Methoden, z. B. durch Behandlung mit einem Silbersalz, überführen. Die so erhaltenen Derivate besitzen besonderen bedeutende physiologische Eigenschaften.If necessary, you can then the halogenated salts thus obtained in Quinoline derivatives with other acid residues by well known methods, e.g. B. by treatment with a silver salt, transferred. The so obtained Derivatives have particularly important physiological properties.
Die folgenden Beispiele zeigen die praktische Anwendung der Erfindung, ohne sie zti beschränken. Beispiel 1 Man erhitzt eine Mischung von 14,59 8-Oxychinolin und 10,1 9 i, 3-Dibrompropan 16 Stunden auf dem Wasserbad. Man löst die klasse in 6o ccm Wasser, behandelt mit Aktivkohle, verdampft zur Trockne und kristallisiert aus ioo ccm Alkohol um. Man erhält gelbe Kristalle vom Dibromhydrat des 1, 3-(8', 8"-Dioxychinolinium)-propans, das bei 192° schmilzt (Block Maquenne).The following examples show the practical application of the invention without restricting it in any way. Example 1 A mixture of 14.59 8-hydroxyquinoline and 10.1 9 i, 3-dibromopropane 16 hours the water bath. The class is dissolved in 60 cc of water, treated with activated charcoal, evaporated to dryness and recrystallized from 100 cc of alcohol. Yellow crystals are obtained from the dibromohydrate of 1,3- (8 ', 8 "-dioxyquinolinium) propane, which melts at 192 ° (block Maquenne).
Man erhält auf die gleiche Weise mit dem 1, 4-Dibrombutan das Dibromhydrat des 1, 4-(8', 8"-DioXychinolinium)-butans (F. = 2o8 bis 21o°, Block Maquenne) und mit dem 1, 5-Dibrompentan das Dibromhvdrat des 1, 5-(8', 8"-Dioxychinolinium)-pentans (F. = 2g5°, Block Maquenne). Beispiel 2 Wenn man das im vorhergehenden Beispiel erwähnte 8-Oxychinolin durch das 8-Methoxychinolin ersetzt, so erhält man auf die gleiche Weise das Dibromhydrat des 1, 3-(8', 8"-Dimethoxychinolinium)-propans, welches nach dem Umkristallisieren aus Wasser bei 21o° schmilzt (Block Maquenne). Beispiel 3 Man erhitzt eine Mischung von 3,6 g 6-Oxychinolin und g,i g i, 3-Dibrompropan 18 Stunden auf dem Wasserbad. Man löst die Masse in 5o ccm Wasser, behandelt mit Aktivkohle und konzentriert. Nach einer mehrmaligen Umkristallisation aus Wasser erhält man gelbe Kristalle vom Dibromhydrat des 1, 3-(6', 6"-Dioxycliinolinium)-propans (F. = 244°, Block Maquenne). Beispiel 4 Man erhitzt 3,6 g 1, 5-Di-[chinolyl-(8')-oxy]-pentan (hergestellt nach Patent 824 343) mit 2,3 g 1, 5-Dibrompentan und 5 ccm absolutem Alkohol 5 Stunden auf dem Wasserbad. Man löst die erhaltene Masse in 30 ccm Wasser, behandelt mit Aktivkohle und verdampft zur Trockne. Der Rückstand wird in einer minimalen Menge Alkohol gelöst und mit Äther ansgefällt.In the same way, with the 1,4-dibromobutane, the dibromohydrate of 1,4 (8 ', 8 "-DioXychinolinium) -butane (F. = 2o8 to 21o °, block Maquenne) and with the 1, 5- Dibromopentane the dibromohydrate of 1, 5- (8 ', 8 "-Dioxyquinolinium) pentane (F. = 2g5 °, Block Maquenne). Example 2 If the 8-oxyquinoline mentioned in the previous example is replaced by 8-methoxyquinoline, the dibromohydrate of 1,3 (8 ', 8 "-dimethoxyquinolinium) propane is obtained in the same way, which after recrystallization Water melts at 210 ° (Maquenne block) Example 3 A mixture of 3.6 g of 6-oxyquinoline and g, igi, 3-dibromopropane is heated on a water bath for 18 hours, and the mass is dissolved in 50 cc of water, treated with activated charcoal After repeated recrystallization from water, yellow crystals of the dibromohydrate of 1,3- (6 ', 6 "-dioxycliinolinium) propane (mp = 244 °, block Maquenne) are obtained. Example 4 3.6 g of 1,5-di- [quinolyl- (8 ') - oxy] -pentane (prepared according to patent 824,343) are heated with 2.3 g of 1,5-dibromopentane and 5 cc of absolute alcohol for 5 hours on the water bath. The mass obtained is dissolved in 30 cc of water, treated with activated charcoal and evaporated to dryness. The residue is dissolved in a minimal amount of alcohol and precipitated with ether.
Man erhält so eine hellgelbe Substanz, welche der Formel entspricht und bei 12o° schmilzt (Block Maquenne). Auf die gleiche Weise erhält man mit dem 1, 6-Dibromhexan und dem i, 6-Di--'chinolyl-(8')-ox,1]-hexan das der vorhergehenden Formel entsprechende Produkt, bei dem jedoch die ('Truppe -(CH,),- durch die Gruppe -(CH,)"- ersetzt ist (F. = I14°, Block Maquenne).A light yellow substance is obtained in this way, which has the formula and melts at 12o ° (Maquenne block). In the same way, with the 1,6-dibromohexane and the 1,6-di- 'quinolyl- (8') - ox, 1] -hexane, the product corresponding to the preceding formula is obtained, but in which the ('troop - (CH,), - is replaced by the group - (CH,) "- (F. = I14 °, Block Maquenne).
Beispiel 6 Man erhitzt eine Mischung von 3,6 6-Oxychinolin, 3 g 1, 6-Dibromhexan und 15 ccm Benzylalkohol 36 Stunden auf i5o@. Man nimmt in 5o ccm siedendem Wasser und 2 g Aktivkohle auf. Man filtriert heiß und läßt durch Abkühlen auskristallisieren. Die erhaltenen Kristalle werden aus 40 ccm absolutem Alkohol und 40 ccm wasserfreiem Äther umkristallisiert. Man erhält so das Dibromhvdrat des 1, 6-(6', 6"-Dioxvchinolinium)-hexans, das bei 2.50- schmilzt (Bleck Maquenne, augenblicklich). Beispiel 6 Wenn man im Beispiel 3 das 6-Oxvchinolin durch die äquimolekulare Menge von 6-Methoxychinolin ersetzt, so erhält man das Dibromhvdrat des i, fi-(6', 6"-Dimethoxychinolinium)-liexans, das bei 146 bis 147" schmilzt (Block Maquenne). Beispiel Wenn man im Beispiel f> das i, 6-Dibromliexan durch die äquivalente molekulare Menge von 1, 4-Dibrombutan ersetzt, so erhält plan das Dibromhydrat des 1, 4-(6', 6"-Dimethoxychinolinium)-btitans, das bei 318° schmilzt (Block Maquenne).EXAMPLE 6 A mixture of 3,6 6-oxyquinoline, 3 g of 1,6-dibromohexane and 15 cc of benzyl alcohol is heated to 150 for 36 hours. It is taken up in 50 cc of boiling water and 2 g of activated charcoal. It is filtered hot and allowed to crystallize out by cooling. The crystals obtained are recrystallized from 40 cc of absolute alcohol and 40 cc of anhydrous ether. This gives the dibromohydrate of 1,6 (6 ', 6 "-dioxyquinolinium) -hexane, which melts at 2.50- (Bleck Maquenne, instantaneous). Example 6 If in Example 3 the 6-oxyquinoline is replaced by the equimolecular amount of Replacing 6-methoxyquinoline, one obtains the dibromohydrate of the i, fi- (6 ', 6 "-dimethoxyquinolinium) -liexane, which melts at 146 to 147" (block Maquenne) -Dibromliexane replaced by the equivalent molecular amount of 1,4-dibromobutane, so plan receives the dibromohydrate of 1,4 (6 ', 6 "-Dimethoxychinolinium) -btitans, which melts at 318 ° (block Maquenne).
Beispiel 8 Wenn man das 1, 4-Di--chinolvl-(8')-oxy]-butan mit dem
i, 5-Dibrompentan kondensiert, so erhält man ein Produkt der folgenden Formel
das bei 198° schmilzt (Block Maduenn(,). Beispiel <l Wenn man das 1, 6-Di-' cliinolyl-(8')-oxy]-1>ent<iii
mit dem 1, 4-Dibrombutan kondensiert, so erhält man eine Verbindung der folgenden
Formel
Claims (1)
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
FR828248X | 1946-10-16 |
Publications (1)
Publication Number | Publication Date |
---|---|
DE828248C true DE828248C (en) | 1952-01-17 |
Family
ID=9283665
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
DES17759A Expired DE828248C (en) | 1946-10-16 | 1950-07-20 | Process for the preparation of new quaternary quinoline derivatives |
Country Status (1)
Country | Link |
---|---|
DE (1) | DE828248C (en) |
-
1950
- 1950-07-20 DE DES17759A patent/DE828248C/en not_active Expired
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