DD242806A1 - PROCESS FOR THE PREPARATION OF 3,4-DIAMINO-CHINOLIN-2-ONEN - Google Patents

PROCESS FOR THE PREPARATION OF 3,4-DIAMINO-CHINOLIN-2-ONEN Download PDF

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Publication number
DD242806A1
DD242806A1 DD28302285A DD28302285A DD242806A1 DD 242806 A1 DD242806 A1 DD 242806A1 DD 28302285 A DD28302285 A DD 28302285A DD 28302285 A DD28302285 A DD 28302285A DD 242806 A1 DD242806 A1 DD 242806A1
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German Democratic Republic
Prior art keywords
quinol
diamino
ones
general formula
preparation
Prior art date
Application number
DD28302285A
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German (de)
Inventor
Harry Schaefer
Karl Gewald
Peter Bellmann
Dieter Lohmann
Gunter Laban
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Univ Dresden Tech
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Priority to DD28302285A priority Critical patent/DD242806A1/en
Publication of DD242806A1 publication Critical patent/DD242806A1/en

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  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)

Abstract

Die Titelverbindungen, die als Zwischenprodukte Verwendung finden koennen, werden erfindungsgemaess durch einfaches Verfahren zugaenglich gemacht, indem 1-(4-Amino-2-oxo-1,2-dihydrochinol-3-yl)-pyridiniumsalze mit 35-45prozentigem, waessrigem Hydrazinhydrat behandelt werden.The title compounds, which can be used as intermediates, are made accessible by a simple process according to the invention by treating 1- (4-amino-2-oxo-1,2-dihydroquinol-3-yl) -pyridinium salts with 35-45% aqueous hydrazine hydrate become.

Description

wodurch R1 und R2 ein Wasserstoff- oder Halogenatom sowie eine Alkyl-, Alkoxy- oder Nitrogruppe sein kann, hergestellt werden, indem 1-(4-Amino-2-oxo-1,2-dihydro-chinol-3-yl)-pyridiumsalze der allgemeinen Formel II,whereby R 1 and R 2 can be a hydrogen or halogen atom and also an alkyl, alkoxy or nitro group, can be prepared by reacting 1- (4-amino-2-oxo-1,2-dihydro-quinol-3-yl) pyridium salts of general formula II,

IlIl

in der R1 und R2 die oben angegebene Bedeutung besitzen und X ein Halogenatom darstellt, in wäßriger Lösung mit einem Amin, vorzugsweise Hydrazinhydrat, behandelt werden.in which R 1 and R 2 have the abovementioned meaning and X represents a halogen atom, are treated in aqueous solution with an amine, preferably hydrazine hydrate.

Die benötigten Ausgangsv.erbindungen I können nach DDR-Patent 142877 (1980), C. A. 95 (1981) P97610w hergestellt werden.The required starting compounds I can be prepared according to DDR patent 142877 (1980), C.A. 95 (1981) P97610w.

Ausführungsbeispieleembodiments Beispiel 1example 1

3,4-Diamino-chinol-2-on3,4-Diamino-quinol-2-one

20mmol i-^-Amino^-oxo-i^-dihydrochinol-S-yO-pyridiniumchlorid werden in 15-2OmI 35%igem wäßrigem Hydratzinhydrat 10 Minuten zum Sieden erhitzt.20 mmol i - ^ - amino ^ -oxo-i ^ -dihydroquinoline-S-yO-pyridinium chloride are heated in 15-2OmI 35% aqueous Hydratzinhydrat for 10 minutes to boiling.

Nach dem Erkalten reibt man an und saugt nach beendeter Kristallisation, die etwa 2 Stunden dauert, ab. Es wird mit Wasser gewaschen und aus Ethanol umkristallisiert. Ausbeute 74%. Farblose Kristalle, die sich ab 2650C zersetzen.After cooling, one rubs on and sucks after completion of crystallization, which lasts about 2 hours. It is washed with water and recrystallized from ethanol. Yield 74%. Colorless crystals that decompose from 265 ° C.

Beispiel 2Example 2

3,4-Diamino-6,7-dimethoxy-chinol-2-on3,4-Diamino-6,7-dimethoxy-quinol-2-one

20mmol 1-(4-Amino-6,7-dimethoxy-2-oxo-1,2-dihydrochinol-3-yl)-pyridiniumchlorid werden in 15-2OmI 35%igem wäßrigem Hydrazinhydrat 20 Minuten zum Sieden erhitzt. Nach dem Erkalten saugt man ab und wäscht mit Wasser. Ausbeute 68%. Das Produkt zersetzt sich ab 25O0C.20 mmol of 1- (4-amino-6,7-dimethoxy-2-oxo-1,2-dihydro-quinol-3-yl) -pyridinium chloride are heated in 15-2OmI 35% aqueous hydrazine hydrate for 20 minutes to boiling. After cooling, it sucks and washes with water. Yield 68%. The product decomposes from 25O 0 C.

Beispiel 3Example 3

3,4-Diamino-6-nitro-chinol-2-on3,4-diamino-6-nitro-quinol-2-one

lOmmol 1-(4-Amino-6-nitro-2-oxo-1,2-dihydrochinol-3-yl)-pyridiniumchlorid erhitzt man in 10ml 35%igem wäßrigem Hydratzinhydrat 2 Std. zum Sie'den. Nach dem Erkalten wird abgesaugt, mit Wasser gewaschen und aus Dimethylformamid umkristallisiert. Ausbeute 79%. Das Produkt zersetzt sich ab 34O0C.1 mmol of 1- (4-amino-6-nitro-2-oxo-1,2-dihydro-quinol-3-yl) -pyridinium chloride is heated in 10 ml of 35% strength aqueous hydrazine hydrate for 2 hours to remove the powder. After cooling, it is filtered off, washed with water and recrystallized from dimethylformamide. Yield 79%. The product decomposes from 34O 0 C.

Claims (2)

Erfindungsanspruch:Invention claim: 1. Verfahren zur Herstellung von 3,4-Diamino-chinol-2-onen der allgemeinen Formel I,1. A process for the preparation of 3,4-diamino-quinol-2-ones of the general formula I, worin R1 und R2 ein Wasserstoff- oder Halogenatom sowie eine Alkyl-, Alkoxy- oder Nitrogruppe sein kann, gekennzeichnet dadurch, daß 1-(4-Amino-2-oxo-1,2-dihydrochinol-3-yl)-pyridiniumsalze der allgemeinen Formel II,wherein R 1 and R 2 may be a hydrogen or halogen atom and an alkyl, alkoxy or nitro group, characterized in that 1- (4-amino-2-oxo-1,2-dihydroquinol-3-yl) pyridinium salts the general formula II, IIII worin R1 und R2 die oben angegebene Bedeutung besitzen und X ein Halogenatom darstellt, mit Aminen in wäßriger Lösung umgesetzt werden.wherein R 1 and R 2 have the meaning given above and X represents a halogen atom, are reacted with amines in aqueous solution. 2. Verfahren nach Punkt 1, gekennzeichnet dadurch, daß als Amin vorzugsweise 35-45%tiges, wäßriges Hydrazinhydrat verwendet wird.2. The method according to item 1, characterized in that is preferably used as the amine 35-45% tiger, aqueous hydrazine hydrate. Anwendungsgebiet der ErfindungField of application of the invention Die Erfindung betrifft ein Verfahren zur Herstellung von 3,4-Diamino-chinol-2-onen. Diese Verbindungen können als Zwischenprodukte für die Herstellung von Wirkstoffen Bedeutung erlangen.The invention relates to a process for the preparation of 3,4-diamino-quinol-2-ones. These compounds can gain importance as intermediates for the production of active ingredients. Charakteristik der bekannten technischen LösungenCharacteristic of the known technical solutions Es ist bekannt, daß nach J. Heterocycl. Chem. 1981,1061, substituierte 3-Amino-chinol-2-one aus 2-Oxo-1,2-dihydro-chinol-3-ylpyridiniumsalzen entstehen, indem letztere mit Anilin behandelt werden. Daraus geht jedoch nichthervor, ob auf ähnliche Weise auch 3,4-Diamino-chinolone hergestellt werden können und insbesondere nicht, welche, im Vergleich zum Anilin besser zu handhabenden Basen geeignet sind.
3,4-Diamino-chinol-2-one sind bislang in der Literatur nicht beschrieben worden.It is known that according to J. Heterocycl. Chem. 1981, 1061, substituted 3-amino-quinol-2-ones are formed from 2-oxo-1,2-dihydro-quinol-3-yl-pyridinium salts by treating the latter with aniline. However, this does not indicate whether 3,4-diamino-quinolones can be prepared in a similar manner, and in particular not, which are more suitable than aniline bases.
3,4-diamino-quinol-2-ones have hitherto not been described in the literature. Ziel der ErfindungObject of the invention Ziel der Erfindung ist es, bisher unbekannte 3,4-Diamino-chinol-2-one in einfacher Weise herzustellen.The aim of the invention is to produce hitherto unknown 3,4-diamino-quinol-2-ones in a simple manner. Darlegung des Wesens der ErfindungExplanation of the essence of the invention Aufgabe der Erfindung ist es, 3,4-Diamino-chinol-2-one durch ein einfaches und neues Verfahren herzustellen. Erfindungsgemäß wird die Aufgabe dadurch gelöst, daß 3,4-Diamino-chinol--one der allgemeinen Formel I,The object of the invention is to produce 3,4-diamino-quinol-2-ones by a simple and novel process. According to the invention the object is achieved in that 3,4-diamino-quinol - one of the general formula I,
DD28302285A 1985-11-20 1985-11-20 PROCESS FOR THE PREPARATION OF 3,4-DIAMINO-CHINOLIN-2-ONEN DD242806A1 (en)

Priority Applications (1)

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DD28302285A DD242806A1 (en) 1985-11-20 1985-11-20 PROCESS FOR THE PREPARATION OF 3,4-DIAMINO-CHINOLIN-2-ONEN

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DD28302285A DD242806A1 (en) 1985-11-20 1985-11-20 PROCESS FOR THE PREPARATION OF 3,4-DIAMINO-CHINOLIN-2-ONEN

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Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0389302A1 (en) 1989-03-23 1990-09-26 Riker Laboratories, Inc. Olefinic 1H-imidazo [4,5-c]quinolin-4-amines
US4988815A (en) * 1989-10-26 1991-01-29 Riker Laboratories, Inc. 3-Amino or 3-nitro quinoline compounds which are intermediates in preparing 1H-imidazo[4,5-c]quinolines

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0389302A1 (en) 1989-03-23 1990-09-26 Riker Laboratories, Inc. Olefinic 1H-imidazo [4,5-c]quinolin-4-amines
US4988815A (en) * 1989-10-26 1991-01-29 Riker Laboratories, Inc. 3-Amino or 3-nitro quinoline compounds which are intermediates in preparing 1H-imidazo[4,5-c]quinolines

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