DE670920C - Process for the preparation of 3,4,5-triaminopyridine - Google Patents

Process for the preparation of 3,4,5-triaminopyridine

Info

Publication number
DE670920C
DE670920C DEB177308D DEB0177308D DE670920C DE 670920 C DE670920 C DE 670920C DE B177308 D DEB177308 D DE B177308D DE B0177308 D DEB0177308 D DE B0177308D DE 670920 C DE670920 C DE 670920C
Authority
DE
Germany
Prior art keywords
triaminopyridine
preparation
aminopyridine
nickel
dinitro
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
Application number
DEB177308D
Other languages
German (de)
Inventor
Dr Hans Hatzig
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Roche Diagnostics GmbH
CF Boehringer und Soehne GmbH
Original Assignee
Boehringer Mannheim GmbH
CF Boehringer und Soehne GmbH
Priority date (The priority date 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 date listed.)
Filing date
Publication date
Application filed by Boehringer Mannheim GmbH, CF Boehringer und Soehne GmbH filed Critical Boehringer Mannheim GmbH
Priority to DEB177308D priority Critical patent/DE670920C/en
Application granted granted Critical
Publication of DE670920C publication Critical patent/DE670920C/en
Expired legal-status Critical Current

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
    • C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
    • C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
    • C07D213/60—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen 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
    • C07D213/72—Nitrogen atoms
    • C07D213/73—Unsubstituted amino or imino radicals

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Pyridine Compounds (AREA)

Description

Verfahren zur Darstellung von 3, 4, 5 -Triaminopyridin Das 3, 4, 5-Triaminopyridin ist bisher noch nicht dargestellt worden. Ein dafür geeigneter Ausgangsstoff ist das auf verschiedenen Wegen zugängliche 3, 5-Dinitro-4-aminopyridin. Bei der Reduktion dieser Verbindung mittels Zinnchlorür und Salzsäure erhält man aber nur ein halogeniertes Produkt, das 2, 6-Chlor-3, 4, 5-triaminopyridin.Method for the preparation of 3, 4, 5-triaminopyridine Das 3, 4, 5-triaminopyridine has not yet been shown. A suitable starting material is 3, 5-dinitro-4-aminopyridine, which is accessible in various ways. In the reduction this compound by means of tin chloride and hydrochloric acid, however, only gives a halogenated one Product, the 2, 6-chloro-3, 4, 5-triaminopyridine.

Es wurde nun gefunden, daß die Darstellung des 3, 4, 5-Triaminopyridins gelingt, wenn man 3, 5-Dinitro-4-aminopyridin mit Nickel katalytisch reduziert.It has now been found that the representation of 3, 4, 5-triaminopyridine succeeds if 3, 5-dinitro-4-aminopyridine is catalytically reduced with nickel.

Die Hydrierung wird in Gegenwart eines geeigneten organischen Lösungsmittels, beispielsweise Äthylalkohol, zweckmäßig in der Wärme und bei einem geringen Überdruck durchgeführt. Das Hydrierungsprodukt kann nach Entfernung des Katalysators und allenfalls vorhandener Verunreinigungen durch Abdampfen des Lösungsmittels gewonnen und z. B. aus einem Alkohol-Benzol-Gemisch umkristallisiert werden. Die neue Verbindung, welche sich vor den bekannten Aminoverbindungen des Pyridins durch ihre erhöhte Basizität auszeichnet, soll zur Herstellung von Heilmitteln verwendet werden.The hydrogenation is carried out in the presence of a suitable organic solvent, for example ethyl alcohol, expediently in the heat and at a slight overpressure carried out. The hydrogenation product can after removal of the catalyst and possibly existing impurities obtained by evaporation of the solvent and z. B. be recrystallized from an alcohol-benzene mixture. The new connection which increased before the known amino compounds of pyridine by their Basicity, is said to be used in the manufacture of remedies.

Beispiele .Examples.

i. Zu 4 g 3, 5-Dinitro-4-aminopyridin, welche in ioo ccm Äthylalkohol gelöst sind, werden 7 g fein verteiltes 2'ickel,' erhalten durch Reduktion von aus Nickelcarbonat gewonnenem Nickeloxyd, zugegeben. Man erwärmt nun auf etwa 9o ° und führt bei dieser Temperatur und etwa 2 Atm. Überdruck so lange Wasserstoff zu, bis ungefähr die theoretische Menge aufgenommen ist. Nach dem Erkalten wird vom ausgeschiedenen Katalysator abfiltriert. Nach Entfernung etwa vorhandener Verunreinigungen durch Ausfüllen mittels Äther wird das Lösungsmittel abgedampft und das dabei zurückbleibende Rohprodukt aus einem Gemisch von Alkohol und Benzol umkristallisiert. Man erhält das 3, 4, 5-Triaminopyridin, welet.es bei 175 ° schmilzt.i. To 4 g of 3,5-dinitro-4-aminopyridine, which are dissolved in 100 cc of ethyl alcohol, 7 g of finely divided nickel, obtained by reducing nickel oxide obtained from nickel carbonate, are added. It is now heated to about 90 ° and is carried out at this temperature and about 2 atm. Hydrogen overpressure until approximately the theoretical amount has been absorbed. After cooling, the precipitated catalyst is filtered off. After any impurities have been removed by filling with ether, the solvent is evaporated and the remaining crude product is recrystallized from a mixture of alcohol and benzene. The 3, 4, 5-triaminopyridine is obtained, welet.es melts at 175 °.

2. 4 g 3, 5-Dmitro-4-aminopyridin werden in 150 ccm Äthylätber gelöst; man gibt äo g fein verteiltes Nickel zu und leitet in das auf 35' erwärmte Reaktionsgemisch so lange Wasserstoff ein, bis ungefähr die theoretische Menge aufgenommen ist. Dann wird von ausgeschiedenem Katalysator und in Äther unlöslichen Verunreinigungen abfiltriert. Das Filtrat wird zur Trockne eingedampft und das dabei zurückbleibende 3, 4, 5-Triaminopyridin, wie in Beispiel i beschrieben, aufgearbeitet.2. 4 g of 3,5-dmitro-4-aminopyridine are dissolved in 150 cc of ethyl ether; one adds equal to g of finely divided nickel and introduces hydrogen into the reaction mixture, which has been heated to 35 ' , until approximately the theoretical amount has been absorbed. Then precipitated catalyst and ether-insoluble impurities are filtered off. The filtrate is evaporated to dryness and the remaining 3, 4, 5-triaminopyridine is worked up as described in Example i.

Claims (3)

PATCNTANsrrÜcEIn: x. Verfahren zur Darstellung von 3, 4, 5- Triäminopyridin, dadurch gekennzeichnet, daß man 3, 5-Dinitro-4-aminopyridin mit Nickel in einem organischen Lösungsmittel katalytisch reduziert. PATCNTANsrRÜcEIn: x. Process for the preparation of 3, 4, 5- triaminopyridine, characterized in that one 3, 5-dinitro-4-aminopyridine with nickel in one Catalytically reduced organic solvents. 2. Verfahren gemäß Anspruch i, dadurch gekennzeichnet, daß man die Reduktion in alkoholischer Lösung vornimmt. 2. The method according to claim i, characterized in that the reduction is carried out in alcoholic solution. 3. Verfahren gemäß Anspruch x und 2, dadurch gekennzeichnet, daß man dieReduktion bei erhöhter Temperatur und einem geringen Überdruck vornimmt:3. The method according to claim x and 2, characterized in that the reduction at an elevated temperature and a slight overpressure:
DEB177308D 1937-02-10 1937-02-10 Process for the preparation of 3,4,5-triaminopyridine Expired DE670920C (en)

Priority Applications (1)

Application Number Priority Date Filing Date Title
DEB177308D DE670920C (en) 1937-02-10 1937-02-10 Process for the preparation of 3,4,5-triaminopyridine

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
DEB177308D DE670920C (en) 1937-02-10 1937-02-10 Process for the preparation of 3,4,5-triaminopyridine

Publications (1)

Publication Number Publication Date
DE670920C true DE670920C (en) 1939-01-27

Family

ID=7008158

Family Applications (1)

Application Number Title Priority Date Filing Date
DEB177308D Expired DE670920C (en) 1937-02-10 1937-02-10 Process for the preparation of 3,4,5-triaminopyridine

Country Status (1)

Country Link
DE (1) DE670920C (en)

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