DE597974C - Verfahren zur Darstellung von substituierten 2-Oxypyridinen - Google Patents

Verfahren zur Darstellung von substituierten 2-Oxypyridinen

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Publication number
DE597974C
DE597974C DEC47632D DEC0047632D DE597974C DE 597974 C DE597974 C DE 597974C DE C47632 D DEC47632 D DE C47632D DE C0047632 D DEC0047632 D DE C0047632D DE 597974 C DE597974 C DE 597974C
Authority
DE
Germany
Prior art keywords
oxy
substituted
preparation
oxypyridines
chloride
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
DEC47632D
Other languages
English (en)
Inventor
Dr Erich Haack
Dr Armin Rost
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.)
Chemische Fabrik Von Heyden AG
Original Assignee
Chemische Fabrik Von Heyden AG
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 Chemische Fabrik Von Heyden AG filed Critical Chemische Fabrik Von Heyden AG
Priority to DEC47632D priority Critical patent/DE597974C/de
Application granted granted Critical
Publication of DE597974C publication Critical patent/DE597974C/de
Expired legal-status Critical Current

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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
    • C07D213/62—Oxygen or sulfur atoms
    • C07D213/63—One oxygen atom
    • C07D213/64—One oxygen atom attached in position 2 or 6
    • 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
    • C07D213/78—Carbon atoms having three bonds to hetero atoms, with at the most one bond to halogen, e.g. ester or nitrile radicals
    • C07D213/79—Acids; Esters
    • C07D213/80—Acids; Esters in position 3
    • 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
    • C07D213/78—Carbon atoms having three bonds to hetero atoms, with at the most one bond to halogen, e.g. ester or nitrile radicals
    • C07D213/81—Amides; Imides
    • C07D213/82—Amides; Imides in position 3
    • 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
    • C07D213/78—Carbon atoms having three bonds to hetero atoms, with at the most one bond to halogen, e.g. ester or nitrile radicals
    • C07D213/84—Nitriles
    • C07D213/85—Nitriles in position 3

Landscapes

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

Description

  • Verfahren zur Darstellung von substituierten 2-Oxypyridinen Durch das Patent 596 728 ist ein Verfahren zur Darstellung von 2-Oxy-5-aminopyridinen geschützt, das dadurch gekennzeichnet ist, daß man 2-Alkoxy-5-aminopyridine mit Halogenwasserstoff entalkyliert.
  • Es wurde nun gefunden, daß sich auch andere Abkömmlinge von 2-Alkoxypyridinen auf diese Weise leicht in die entsprechenden 2-Oxyverbindungen überführen lassen. Da eine Reihe von substituierten 2-Alkoxypyridinen, z. B. die 5-Derivate, leicht und in großer Reinheit zugänglich sind, so bedeutet das Verfahren einen großen technischen Fortschritt, der noch durch die Tatsache erhöht wird, daß die Oxyverbindungen entweder praktisch rein oder nur mit geringfügigen und leicht zu entfernenden Mengen von Katalysatorstoffen vermischt, anfallen. Beispiel i 2-Oxy-5-nitropyridin zoo g 2-Äthoxy-5-nitropyridin (dargestellt nach Patentschrift 568 549) werden mit einigen Grammen wasserfreiem Zinkchlorid auf etwa =6o° erhitzt. In die geschmolzene Masse leitet man so lange trockenen Chlorwasserstoff ein, bis kein Chloräthyl mehr entweicht. Die abgekühlte hellgelbe Schmelze kann entweder ohne jede Reinigung weiterverarbeitet werden (z. B. zu 2-Chlor-5-nitropyridin) oder aber mit heißem Wasser vom Zinkchlorid befreit werden. Es bleibt dann praktisch reines 2-Oxy-5-nitropyridin annähernd in der berechneten Menge zurück. Beispiel -2-Oxy-5-cyanpyridin ioo g 2-Äthoxy-5-cyanpyridin (dargestellt aus 2-Äthoxy-5-aminopyridin; F. 98 bis 99°) werden bei ==o° unter gutem mechanischen Rühren mit Chlorwasserstoff behandelt. Die Masse erstarrt nach anfänglichem Schmelzen bald wieder. Wenn kein Chloräthyl mehr entweicht, wird die Chlorwasserstoffzufuhr abgebrochen. Es hinterbleibt praktisch reines 2-Oxy-5-cyanpyridin vom F. z52' in annähernd berechneter Ausbeute. Beispiel 3 2-Oxy-5-pyridyläthylketon 2-Äthoxy-5-pyridyläthylketon (F. 42°) -wird auf ==o° erhitzt und mit trockenem Chlorwasserstoff behandelt. Dieser wird unter Abspaltung von Chloräthyl aufgenommen. Das 2-Oxy-5-pyridyläthylketon bildet ein Hydrochlorid, das bei etwa 1,75' unter Aufschäumen schmilzt. Mit Natriumcarbonat entsteht daraus die freie Base, die aus Wasser in dünnen Nadeln kristallisiert; F. 127 bis i28°. Die Ausbeute ist quantitativ.
  • Beispiel q. 2-Oxy-3, 5-dichlorpyridin In 2 Äthoxy-3,5-dichlorpyridin wird bei Anwesenheit von etwas Zinkchlorid trockene Salzsäure eingeleitet. Von i6o° an wird die Salzsäure unter Abspaltung von Chloräthyl aufgenommen. Es hinterbleibt eine farblose Schmelze, die nach einmaliger Kristallisation aus Eisessigwasser farblose Nadeln vom F. 177 bis 178' in fast vollständiger Ausbeute liefert.
  • Beispiel 5 2-Oxy-3-chlor-5-nitropyridin 2-Äthoxy-3-chlor-5-nitropyridin (F. 7i°) wild bei Anwesenheit von Zinkchlorid mit trockenem Chlorwasserstoff bei 16o bis z7o° entalkyliert. Es entsteht eine gelbliche Kristallmasse; der Schmelzpunkt des Rohprodukts ist 165 bis z67°. . Die Ausbeute ist nahezu vollständig.
  • Beispiel 6 a-Oxypyridin-5-carbonsäureäthylamid 2 -Butyloxypyridin-5 -carbonsäuremonoäthylamid (F. 78 bis 79') «erden bei i2o bis 1:25' mit trockenem Chlorwasserstoff behandelt. Es destilliert x Mol. Butylchlorid ab. Der Rückstand wird mit Natriumcarbonat alkalisch gemacht und mit Chloroform von Verunreinigungen befreit. Aus der wäßrigen Lösung kristallisiert nach einiger Zeit das Oxycarbonsäureamid in großen, klaren Kristallen vom F. 205 bis 2o6°. Die Ausbeute ist unter Berücksichtigung der ziemlich großen Löslichkeit in Wasser fast vollständig. Beispiel 7 2-Oxypyridin-5-carbonsäure 2-Äthoxypyridin-5-carbonsäure wird bei etwa i2o ° mit Chlorwasserstoff behandelt. Unter Abspaltung von Athylchlorid entsteht 2-Oxypyridin-5-carbonsäure (F. 301 bis 3o3°).

Claims (1)

  1. PATENTANSPRUCH Weitere Ausbildung des Verfahrens zur Darstellung von substituierten 2-Oxypyridinen gemäß Patent 596 728, dadurch gekennzeichnet, daß man hier an Stelle der im Hauptpatent genannten 2 Alkoxy-5-aminopyridine andere beliebig substituierte 2-Alkoxypyridine bei erhöhter Temperatur mit Halogenwasserstoff mit oder ohne Verwendung von Katalysatoren spaltet.
DEC47632D 1933-03-10 1933-03-10 Verfahren zur Darstellung von substituierten 2-Oxypyridinen Expired DE597974C (de)

Priority Applications (1)

Application Number Priority Date Filing Date Title
DEC47632D DE597974C (de) 1933-03-10 1933-03-10 Verfahren zur Darstellung von substituierten 2-Oxypyridinen

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
DEC47632D DE597974C (de) 1933-03-10 1933-03-10 Verfahren zur Darstellung von substituierten 2-Oxypyridinen

Publications (1)

Publication Number Publication Date
DE597974C true DE597974C (de) 1934-06-02

Family

ID=7026608

Family Applications (1)

Application Number Title Priority Date Filing Date
DEC47632D Expired DE597974C (de) 1933-03-10 1933-03-10 Verfahren zur Darstellung von substituierten 2-Oxypyridinen

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Country Link
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Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0206293A3 (en) * 1985-06-25 1988-01-20 Lonza Ag Process for the preparation of 3,5-dichloro-2-pyridone

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0206293A3 (en) * 1985-06-25 1988-01-20 Lonza Ag Process for the preparation of 3,5-dichloro-2-pyridone

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