DE2150772A1 - METHOD FOR PREPARING 6-HYDROXY-2-PYRIDONE-3-CARBONIC ACID AMIDE COMPOUNDS - Google Patents

METHOD FOR PREPARING 6-HYDROXY-2-PYRIDONE-3-CARBONIC ACID AMIDE COMPOUNDS

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Publication number
DE2150772A1
DE2150772A1 DE19712150772 DE2150772A DE2150772A1 DE 2150772 A1 DE2150772 A1 DE 2150772A1 DE 19712150772 DE19712150772 DE 19712150772 DE 2150772 A DE2150772 A DE 2150772A DE 2150772 A1 DE2150772 A1 DE 2150772A1
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Prior art keywords
alkyl
hydrogen
condensation
general formula
compound
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German (de)
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Ernst Dr Heinrich
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Cassella Farbwerke Mainkur AG
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Cassella Farbwerke Mainkur AG
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Priority to DE19712150772 priority Critical patent/DE2150772A1/en
Priority to JP10121572A priority patent/JPS4844263A/ja
Priority to GB4687772A priority patent/GB1373314A/en
Priority to FR7235922A priority patent/FR2156231B1/fr
Priority to CH1490172A priority patent/CH568289A5/xx
Publication of DE2150772A1 publication Critical patent/DE2150772A1/en
Pending legal-status Critical Current

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    • 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

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

Description

CASSELLA FARBWERKE MAINKUR 2150772CASSELLA FARBWERKE MAINKUR 2150772

AKTIENGESELLSCHAFTSHARED COMPANY

HEIm Ref HEIm Ref

Frankfurt(Main), den 8. 10. 1971 Dr.Eu/CzFrankfurt (Main), October 8, 1971 Dr.Eu/Cz

Verfahren zur Herstellung von e-Process for the production of e-

carbonsäureamid-Verbindungencarboxamide compounds

Die Erfindung betrifft ein neues Verfahren zur Herstellung von 6-Hydroxy-2-pyridon-3-carbonsäureamid-Verbindungen der allgemeinen FormelThe invention relates to a new method of manufacture of 6-hydroxy-2-pyridone-3-carboxamide compounds of the general formula

in der X Wasserstoff, eine Cyan-, eine Alkoxy-, eine gegebenenfalls verzweigte und/oder substituierte Alkyl-, gegebenenfalls verzweigte und/oder substituierte Alkenyl-, gegebenenfalls substituierte Cycloalkyl-, Aralkyl-, Arylgruppe oder einen heterocyclischen Rest,in which X is hydrogen, cyano, alkoxy, optionally branched and / or substituted alkyl, optionally branched and / or substituted alkenyl, optionally substituted cycloalkyl, aralkyl, aryl or a heterocyclic radical,

Y Wasserstoff, eine gegebenenfalls substituierte Amino-, gegebenenfalls verzweigte und/oder substituierte Alkyl-, gegebenenfalls verzweigte und/oder substituierte Alkenyl-, gegebenenfalls substituierte Cycloalkyl-, Aralkyl- oder Arylgruppe oder einen heterocyclischen Rest,Y is hydrogen, an optionally substituted amino, optionally branched and / or substituted alkyl, optionally branched one and / or substituted alkenyl, optionally substituted cycloalkyl, aralkyl or aryl group or a heterocyclic radical,

R. und/oder B„ Wasserstoff, eine Alkyl-, Hydroxyalkyl-, Alkoxyalkyl-, Cycloalkyl-, Aralkyl- oder Arylgruppe, wobei die Alkylreste R1 und R2 auchR. and / or B “hydrogen, an alkyl, hydroxyalkyl, alkoxyalkyl, cycloalkyl, aralkyl or aryl group, the alkyl radicals R 1 and R 2 also

3 0 9 8 16/1133 ORiGiNAL INSPECTED3 0 9 8 16/1133 ORiGiNAL INSPECTED

- 2 - Ref. 2927- 2 - Ref. 2927

direkt oder über ein Heteroatom verbunden sein können,can be linked directly or via a heteroatom,

bedeuten· Das erfindungsgemäße Verfahren ist dadurch gekennzeichnet, daß entweder eine Verbindung der allgemeinen Formel IIThe method according to the invention is characterized in that that either a compound of the general formula II

ZO-CO- CH2 - CO - X IIZO-CO- CH 2 - CO - X II

worin X die bereits oben angegebene Bedeutung besitzt und Z einen Alleylrest, vorzugsweise mit 1 bis 2 C-Atomen, bedeutet, mit einer Verbindung der allgemeinen Formel IIIwherein X has the meaning already given above and Z is an alleyl radical, preferably with 1 to 2 carbon atoms, means with a compound of the general formula III

HYN - CO - CH0 - CO -HYN - CO - CH 0 - CO -

kondensiert wird, oder daß eine Verbindung der allgemeinen Formel IVis condensed, or that a compound of the general formula IV

HYN - CO - CH2 - CO - X IVHYN - CO - CH 2 - CO - X IV

mit einer Verbindung der allgemeinen Formel Vwith a compound of the general formula V

ZO-CO- CH0 - CO -ZO-CO- CH 0 - CO -

kondensiert wird· In den Formeln III, IV und V besitzen X, Y, R1, R2 und Z die bereits genannte Bedeutung.condensation is carried out · In formulas III, IV and V, X, Y, R 1 , R 2 and Z have the meanings already mentioned.

Als Substituenten für Cycloalkyl- und für Arylgruppen in den Resten X, Y, R1 und R2 kommen beispielsweise ein oder mehrere Halogenatome, Cyan-, Alkyl- oder Alkoxygruppen in Betracht. In den Resten X und Y können die Alkyl- bzw.Suitable substituents for cycloalkyl and aryl groups in the radicals X, Y, R 1 and R 2 are, for example, one or more halogen atoms, cyano, alkyl or alkoxy groups. In the radicals X and Y, the alkyl or

309816/1133309816/1133

- 3 - Ref. 2927- 3 - Ref. 2927

Alkenylgruppen beispielsweise substituiert sein, durch eine Cyan—, Hydroxy—, Acyloxy—j Alkoxy—, Aryloxy— oder eine Alkyl- bzw. Arylamino-carbonyloxy-Gruppe. Ferner auch durch eine Mono- bzw« Dialkylaminogruppe, wobei die Alkylgruppen auch direkt oder über ein Heteroatom verbunden sein können. Bedeutet Y eine Aminogruppe, so kann diese durch Alkylgruppen mono- oder disubstituiert oder durch einen aliphatischen oder aromatischen Säurerest aoyliert sein.Alkenyl groups can be substituted, for example, by a cyano, hydroxy, acyloxy — j alkoxy, aryloxy or an alkyl or arylamino-carbonyloxy group. Further also by a mono- or dialkylamino group, the alkyl groups also directly or via a heteroatom can be connected. If Y is an amino group, this can be mono- or disubstituted by alkyl groups or be aoylated by an aliphatic or aromatic acid radical.

Die Kettenlänge der Alkyl- bzw. Alkenylgruppen in den Resten X und Y beträgt vorzugsweise 1-6 C-Atome« Ein heterocyclischer Rest für X und/oder Y kann beispielsweise eine Pyridyl-, Thiazolyl-, Benzthiazolyl-, Imidazolyl-, Benzimidazolyl-, Thienyl-, Furyl- oder eine Pyrrolylgruppe sein.The chain length of the alkyl or alkenyl groups in the X and Y radicals are preferably 1-6 carbon atoms. A heterocyclic radical for X and / or Y can, for example a pyridyl, thiazolyl, benzthiazolyl, imidazolyl, benzimidazolyl, thienyl, furyl or be a pyrrolyl group.

Als Cycloaikylgruppen kommen beispielsweise Cyclopropylbis Cyclooctylreste, vorzugsweise Cyclopentyl- oder Cyclohexylreste in Betracht.As cycloalkyl groups, for example, cyclopropyl bis cyclooctyl radicals, preferably cyclopentyl or Cyclohexyl radicals into consideration.

Das erfindungsgemäße Verfahren dient hauptsächlich zur Herstellung von Verbindungen, bei denen in der allgemeinen Formel I die Alkylgruppen in den Resten X, Y, R- und R2 1 - k Kohlenstoffatome, insbesondere 1 oder 2 Kohlenstoffatome, besitzen und vorzugsweise zur Herstellung von solchen Verbindungen der allgemeinen Formel I, bei denenThe process according to the invention is mainly used for the preparation of compounds in which in general formula I the alkyl groups in the radicals X, Y, R- and R 2 have 1- k carbon atoms, in particular 1 or 2 carbon atoms, and preferably for the preparation of such compounds of the general formula I, in which

309816/1 133309816/1 133

- k - Ref. 2927- k - Ref. 2927

X einen. AlkyIrest,X one. AlkyIrest, Y Wasserstoff, einen Alkyl- oder Phenylrest,Y is hydrogen, an alkyl or phenyl radical, R. Wasserstoff undR. Hydrogen and R„ Wasserstoff oder einen AlkylrestR “is hydrogen or an alkyl radical

bedeuten, wobei die Alkylreste 1 bis 4 Kohlenstoffatome, insbesondere 1 bis 2 Kohlenstoffatome, besitzen.mean, where the alkyl radicals 1 to 4 carbon atoms, especially 1 to 2 carbon atoms.

Für die 6-Hydroxy-2-pyridon-3-carbonsäureamide der allgemeinen Formel I sind tautomere Formen denkbar, beispielsweise:Tautomeric forms are conceivable for the 6-hydroxy-2-pyridone-3-carboxamides of the general formula I, for example:

HOHO

Y YY Y

Ib IcIb Ic

und falls Y Wasserstoff bedeutet auch noch z.B.and if Y is hydrogen also e.g.

IfIf

309816/ 1309816/1

- 5 - Ref. 2927- 5 - Ref. 2927

Im Rahmen der vorliegenden Anmeldung sollen in der Beschreibung und in den Ansprüchen auch die möglichen tautomeren Formen verstanden sein.In the context of the present application, the description and claims should also include the possible be understood tautomeric forms.

Die erfindungsgemäße Kondensation einer Verbindung der allgemeinen Formel II mit einer Verbindung der allgemeinen Formel III bzw. die Kondensation einer Verbindung der allgemeinen Formel IV mit einer Verbindung der allgemeinen Formel V verläuft unter Austritt des Alkohols ZOH nach folgendem Schema:The inventive condensation of a compound of the general formula II with a compound of the general formula III or the condensation of a compound of the general formula IV with a compound of the general formula V proceeds with the exit of the Alcohol ZOH according to the following scheme:

O=CO = C

H2C-C-N^H 2 CCN ^

ü-N\ü- N \

HYNHYN

IIII

O =0O = 0

IIIIII

• A• A

=0= 0

=c= c

I C=OI C = O

IVIV

Die Kondensation wird vorzugsweise in einem organischen Lösungs- bzw. Verdünnungsmittel in Gegenwart eines alkalischen Kondensationsmittels, zweckmäßigerweise bei Temperaturen von 0 - 1000C1 durchgeführt. Als Lösung·- bzw. Verdünnungsmittel wird vorzugsweise ein niederer Alkohol,The condensation is preferably carried out in an organic solvent or diluent in the presence of an alkaline condensing agent, expediently at temperatures from 0 - 100 0 C performed. 1 The preferred solution or diluent is a lower alcohol,

309816/1133309816/1133

- 6 -> Ref. 2927- 6 - > Ref. 2927

beispielsweise Äthanol, verwendet. Als alkalische Kondensationsmittel sind zum Beispiel Natrium- und Kaliumalkoholate, insbesondere Natrium- und Kalium— äthylat und Natrium- und Kaliumcarbonat zu nennen.for example, ethanol is used. As alkaline Examples of condensation agents are sodium and Potassium alcoholates, especially sodium and potassium to name ethylate and sodium and potassium carbonate.

Es ist bekannt (DOS 2 045 851), 6-Hydroxy-2-pyridon-3-carbonsäureamid-Verbindungen durch Verseifung der entsprechenden 3-Cyan-Verbindungen mittels 94 bis 97#igerIt is known (DOS 2 045 851), 6-hydroxy-2-pyridone-3-carboxamide compounds by saponification of the corresponding 3-cyano compounds using 94 to 97 # iger

Schwefelsäure bei 5O-6O°C herzustellen. Dieses Verfahren liefert aber in vielen Fällen keine reine 6-Hydroxy-2-pyridon-3-carbonsäureamid-Verbindungen, da durch vollständige Verseifung der Nitrtlgruppe zur Carbonsäure und Abspaltung von Kohlensäure die entsprechenden 6—Hydroxy-2—pyridon-Verbindungen mitgebildet werden. Die nach dem erfindungsgemäßen Verfahren dargestellten 6-Hydroxy-2-pyridon-3-carbonsäureamid-Verbindungen besitzen dagegen eine hohe Reinheit.To produce sulfuric acid at 50-60 ° C. This method but in many cases does not provide pure 6-hydroxy-2-pyridone-3-carboxamide compounds, since by complete saponification of the nitrate group to the carboxylic acid and splitting off of carbonic acid the corresponding 6 — hydroxy-2 — pyridone compounds are also formed. the have 6-hydroxy-2-pyridone-3-carboxamide compounds prepared by the process according to the invention on the other hand, a high degree of purity.

Es ist ferner bekannt (U.Basu, Journ.Ind.Chem.Soc.1935» Seite 306), 4-Methyl-6-hydroxy-2-pyridon-3-carbonsäureamid durch Kondensation von ß-Amino-crotonsäureäthylester mit Malonsäurediamid herzustellen. Das erfindungsgemäße Verfahren ist wirtschaftlicher als dieses bekannte Verfahren, da als Ausgangsmaterial zur Herstellung von 4-Methyl-6-hydroxy-2-pyridon-3-carbonsäureamid der Acetessigsäureäthylester als Ausgangsmaterial dient,It is also known (U.Basu, Journ.Ind.Chem.Soc.1935 » Page 306), 4-methyl-6-hydroxy-2-pyridone-3-carboxamide by condensation of ß-amino-crotonic acid ethyl ester with malonic acid diamide. The inventive Process is more economical than this known process because it is used as a starting material for the production of 4-methyl-6-hydroxy-2-pyridone-3-carboxamide of the ethyl acetoacetate is used as the starting material,

309816/ 1 133309816/1 133

- 7 - Ref. 2927- 7 - Ref. 2927

während der ß—Amino—erotonsäureäthylester erst ans: dem Acetessigsäureäthylester mittels Ammoniak hergestellt werden muß.while the ß-amino-erotonic acid ethyl ester only ans: dem Ethyl acetoacetate must be prepared by means of ammonia.

Die nach dem erfindungsgemäßen Verfahren hergestellten Verbindungen sind wertvolle Zwischenprodukte, die insbesondere zur Herstellung von Farbstoffen, vorzugsweise Azofarbstoffen, geeignet sind.The compounds prepared by the process according to the invention are valuable intermediates, in particular for the production of dyes, preferably azo dyes, are suitable.

Beispielexample

Zu einer Lösung aus 6OO Gerichtsteilen Äthylalkohol, 255 Gewichtsteilen Malonsäurediamid und 390 Gewichtsteilen Acetessigsäureäthylester wird in 2 Stunden bei 40-45°C eine Lösung von 210 Gewichtsteilen Ätzkali in 1000 Gewichtsteilen Äthylalkohol einlaufen gelassen. Anschließend wird die Reaktionslösung in 4 Stunden auf 85°C erhitzt und 6 Stunden bei dieser Temperatur gehalten. Dann wird der Äthylalkohol abdestilliert, der Rückstand in 2000 Gewichtsteilen Wasser gelöst und das gebildete ^-Methyl-6-hydroxy-2-pyridon-3-earbonsäureamid durch Versetzen mit 460 Gewichtsteilen Salzsäure 30$ig ausgefällt. Es wird abgesaugt, mit Wasser gewaschen und getrocknet.To a solution of 600 meal parts of ethyl alcohol, 255 parts by weight of malonic acid diamide and 390 parts by weight Ethyl acetoacetate becomes a in 2 hours at 40-45 ° C Solution of 210 parts by weight of caustic potash in 1000 parts by weight of ethyl alcohol run in. Then will the reaction solution is heated to 85 ° C. in 4 hours and kept at this temperature for 6 hours. Then the Ethyl alcohol is distilled off, the residue dissolved in 2000 parts by weight of water and the formed ^ -Methyl-6-hydroxy-2-pyridon-3-carboxamide by adding 460 parts by weight Hydrochloric acid precipitated in 30%. It is filtered off with suction, washed with water and dried.

Analyse: C-HgO5N2 berechnet: 16,7% N.Analysis: C-HgO 5 N 2 calculated: 16.7% N.

gefunden: 16,5% N.found: 16.5% N.

-Die gleiche Verbindung wird erhalten, wenn in dem Beispiel das Malonsäurediamid und der Acetessigsäureäthylester ersetzt werden durch äquimolekulare Mengen von Malonsäuremonoamid-monoäthylester und Acetessigsäureamide-The same connection is obtained when in the example the malonic acid diamide and the ethyl acetoacetate are replaced by equimolecular amounts of monoethyl malonate and acetoacetic acid amides

309816/ 1133309816/1133

Ref. 2927Ref. 2927

In der folgenden Tabelle sind weitere nach dem erfindungsgemäßen Verfahren hergestellte 6-IIydroxy-2-pyridon—3-carbonsäureamide angeführt:In the following table are further according to the invention 6-II-hydroxy-2-pyridone-3-carboxamides made by the process listed:

,R., R.

HOHO

(Io Rs(Io R s

• ί
Y • ί
Y

No. XNo. X

bzw. tautomere Formen·or tautomeric forms

Brutto- Berechnet Gefunden formel # N # NGross Calculated Found formula # N # N

1. -C1. -C

2H5 2 H 5

2. -C3H7(U)2. -C 3 H 7 (U)

-H -II -H C8H10O3N2 -II -H -H C9H12O3N2 -H -II-HC 8 H 10 O 3 N 2 -II -H-HC 9 H 12 O 3 N 2

3. -C3H7(ISo) -H -H -H3. -C 3 H 7 (ISo) -H -H -H

4. -C4H9 (n) -H -H -Π4. -C 4 H 9 (n) -H -H -Π

5. -C4H9(iso) -H -Π -H5. -C 4 H 9 (iso) -H -Π -H

6. -C4H9(SeIi) -H -H -II6. -C 4 H 9 (SeIi) -H -H -II

7. -C2H0(tert) -H -H -H7. -C 2 H 0 (tert) -H-H -H

10. -CII-CH0 "II -TI -II10. -CII-CH 0 "II -TI -II

-CIl"-CIl "

11. -C * -II -II -II11. -C * -II -II -II

CH2 CH 2

12. -CH-CH-CH,. -H -H -H12. -CH-CH-CH ,. -H -H -H

14,3
14,3
13,3
13,3
13,3
13,314.3
14.3
13.3
13.3
13.3
13.3

8. -C5H11CiSo) -H -H -H C11H16O3N2 12,58. -C 5 H 11 CiSo) -H -H-HC 11 H 16 O 3 N 2 12.5

9. -C6H13(n) -II -H -Π C12II18O3N2 11,89. -C 6 H 13 (n) -II -H -Π C 12 II 18 O 3 N 2 11.8

15,615.6

14,414.4

15,6 14,6 14,1 13,7 13,2 13,6 13,015.6 14.6 14.1 13.7 13.2 13.6 13.0

12,9 11,6 1.1S, 2 14,012.9 11.6 1. 1 S, 2 14.0

14,214.2

309M6/ 1133309M6 / 1133

No, XNo, X

R2 Bruttoformel R 2 gross formula

Ref. 2927Ref. 2927

Berechnet GefundenCalculated Found

% N # N % N # N

-H -H -H C6HgO N2 18,2-H -H-HC 6 HgO N 2 18.2

—Η -H —Η CRHinO. Np 14,1-Η -H -Η C R H in O. Np 14.1

-H -H -H C12H16O3N2 11,9-H -H-HC 12 H 16 O 3 N 2 11.9

-H -H -H C13H12O3N2 11,5-H -H-HC 13 H 12 O 3 N 2 11.5

-H -H -H C12H10O3N2 12,2-H -H-HC 12 H 10 O 3 N 2 12.2

18,618.6

14,5 11,714.5 11.7

11,8 11,811.8 11.8

-H -H -H C10H8O4N2 12,7 12,4-H -H-HC 10 H 8 O 4 N 2 12.7 12.4

C CHC CH

20. -CH2-CH2-CN20. -CH 2 -CH 2 -CN

21. -CH2-CH2-OH21. -CH 2 -CH 2 -OH

22. -CH2-CH2-OCH3 -H -H -H C11H9O3N3 18,222. -CH 2 -CH 2 -OCH 3 -H-H -HC 11 H 9 O 3 N 3 18.2

-H -H -H C9H9O3N3 20,3-H -H-HC 9 H 9 O 3 N 3 20.3

-H -H -H C8H10O4N2 14,1-H -H-HC 8 H 10 O 4 N 2 14.1

-H -H -H C9H12O4N2 13,3-H -H-HC 9 H 12 O 4 N 2 13.3

9H12O4N2 9 H 12 O 4 N 2

23.-CH2-CH2-O-CO-CH3 -H -H -23.-CH 2 -CH 2 -O-CO-CH 3 -H -H -

24.-CHgCH2-O-CO-NH-C2H5 -H -H -H C11H15O5N3 15,624.-CHgCH 2 -O-CO-NH-C 2 H 5 -H-H -HC 11 H 15 O 5 N 3 15.6

25, 7H\ CH25, 7H \ CH

-H -H -H 11,1-H -H -H 11.1

CH3 26. /~\__CH, -H -H -H C14H14O3N2 10,9CH 3 26. / ~ \ __ CH, -H -H-HC 14 H 14 O 3 N 2 10.9

18,618.6

20,720.7

13,613.6

11,3 15,211.3 15.2

11,6 10,511.6 10.5

309816/1133309816/1133

- 10 - Ref. 2927- 10 - Ref. 2927

ν η ρ Brutto- Berechnet Gefunden x ttl tt2 formel # N % Nν η ρ gross calculated Found x tt l tt 2 formula # N % N

27. -27.-

28. -28.-

-H -H -H C13H20O3N2 11,1-H -H-HC 13 H 20 O 3 N 2 11.1

-H -H -H-H -H -H

29. -C8H17(SeIc) -H29. -C 8 H 17 (SeIc) -H

30. -C8H17(iso) -H30. -C 8 H 17 (iso) -H

31. -C17H35(n) -H31. -C 17 H 35 (n) -H

32. -CH3 -CH3 32. -CH 3 -CH 3

33. -C2H5 -CH3 33. -C 2 H 5 -CH 3

34. -C3H7(n) -CH3 34. -C 3 H 7 (n) -CH 3

35. -C3H7(ISo) -CH3 35. -C 3 H 7 (ISo) -CH 3

36. -C4H9(n) -CH3 36. -C 4 H 9 (n) -CH 3

37. -C4H9(ISo) -CH3 37. -C 4 H 9 (ISo) -CH 3

38. -C4H9(SeIc) -CH3 38. -C 4 H 9 (SeIc) -CH 3

39. -C.Ho(tert) -CH,39. -CH o (tert) -CH,

40. -40. -

-CH-CH

41. -C6H13 (n) -CH3 41. -C 6 H 13 (n) -CH 3

42. -C7H15 (n) -CH3 42. -C 7 H 15 (n) -CH 3

43. -C7H15(ISo) -CH3 43. -C 7 H 15 (ISo) -CH 3

44. -C8H17(SeIc) -CH3 44. -C 8 H 17 (SeIc) -CH 3

45. -C8H17(ISo) -CH3 45. -C 8 H 17 (ISo) -CH 3

46. -C17H35(n) -CH3 46. -C 17 H 35 (n) -CH 3

-H-H

-H -H -H -H -H -H-H -H -H -H -H -H

-H -H -H -H -H -H -H -H -H -H -H-H -H -H -H -H -H -H -H -H -H -H

-H-H

-H-H

-H-H

-H 11,1-H 11.1

-H C14H22°3N2 10'5 - HC 14 H 22 ° 3 N 2 10 ' 5

-H » 10,5-H »10.5

-H C23H40O3N2 7,1-HC 23 H 40 O 3 N 2 7.1

-H C8H10O3N2 15,4-HC 8 H 10 O 3 N 2 15.4

-H C9H12O3N2 14,3-HC 9 H 12 O 3 N 2 14.3

-H C10II14O3N2 13,3-HC 10 II 14 O 3 N 2 13.3

-H · 13,3-H · 13.3

12,5
12/5
12,5
12,512.5
12/5
12.5
12.5

-H C12H18O3N2 11,8-HC 12 H 18 O 3 N 2 11.8

-H C13H20O3N2 11,1
-H C14H22O3N2 10,5
-H " 10,5-HC 13 H 20 O 3 N 2 11.1
-HC 14 H 22 O 3 N 2 10.5
-H "10.5

H C15H24O3N2 10,0
H n 10,oHC 15 H 24 O 3 N 2 10.0
H n 10, o

H C24H42O3N2 6,9HC 24 H 42 O 3 N 2 6.9

11,6 11,4 10,1 10,3 6,9 15,7 14,8 13,0 13,611.6 11.4 10.1 10.3 6.9 15.7 14.8 13.0 13.6

12,3 12,212.3 12.2

12,712.7

12,112.1

12,0 11,6 10,0 10,712.0 11.6 10.0 10.7

10,5 10,710.5 10.7

309816/1133309816/1133

R. R„ Bruttoformel R. R "Gross formula

Ref. 2927Ref. 2927

Berechnet GefundenCalculated Found

$ N # N $ N # N

47. -CH=CH2 47. -CH = CH 2

48. -48.-

^ cn=cnf ^ cn = cn f

49. -CH=CH-Cl49. -CH = CH-Cl

50. -CH=Cl2 50. -CH = Cl 2

-H-H

56. -CH2-CH2-OH -H -H C9H10O3N2 14,456. -CH 2 -CH 2 -OH -H-HC 9 H 10 O 3 N 2 14.4

-CH3 -H -H C10H12O3N2 13,5-CH 3 -H-HC 10 H 12 O 3 N 2 13.5

-CH3 -H -H C9II9O3N2Cl 12,3-CH 3 -H-HC 9 II 9 O 3 N 2 Cl 12.3

-CH3 -H -H C9H8O3N2Cl2 10,7-CH 3 -H -HC 9 H 8 O 3 N 2 Cl 2 10.7

51. -Cn=CH-CH3 -CH3 -H -H C10H12O3N2 13,551. -Cn = CH-CH 3 -CH 3 -H -HC 10 H 12 O 3 N 2 13.5

-CH3 -H -H C7H8O3N2 16,7-CH 3 -H-HC 7 H 8 O 3 N 2 16.7

-CH3 -H -H C13H18O3N2 11,2-CH 3 -H-HC 13 H 18 O 3 N 2 11.2

-CH3 -H -H C14H14O3N2 10,9-CH 3 -H-HC 14 H 14 O 3 N 2 10.9

55. -CH2-CH2-CN -CH3 -H -H C10H11O3N3 19,055. -CH 2 -CH 2 -CN -CH 3 -H -HC 10 H 11 O 3 N 3 19.0

-CH3 -H -H C9H12O4N2 13,3-CH 3 -H-HC 9 H 12 O 4 N 2 13.3

57. -CH2-CH2-OCH3 -CH3 -H -H C10H14O4N2 12,457. -CH 2 -CH 2 -OCH 3 -CH 3 -H -HC 10 H 14 O 4 N 2 12.4

58.-CH2-CH2-O-CO-CH3 -CH3 -H -H58.-CH 2 -CH 2 -O-CO-CH 3 -CH 3 -H -H

59. -/πΛ—OCH3 59. - / πΛ-OCH 3

60. J/ V-Cl60. J / V-Cl

01. jT\ 01. jT \

Ga. -CH2- f y Ga. -CH 2 - fy

-CH3 -H -H-CH 3 -H -H

11,011.0

10,010.0

-H -H C13H31O3N2Cl 10,1-H-HC 13 H 31 O 3 N 2 Cl 10.1

-CH, -H -H C1-H19O-Np 11,5-CH, -H-HC 1 -H 19 O-Np 11.5

13H12O3N2 13 H 12 O 3 N 2

CH3 -Π -HCH 3 -Π -H

14,2 13,814.2 13.8

12,7 11,2 13,8 17,1 11,512.7 11.2 13.8 17.1 11.5

11,511.5

19,4 13,0 12,0 11,5 10,719.4 13.0 12.0 11.5 10.7

10,5 11,810.5 11.8

10,3 . 10,510.3. 10.5

0 9; 16/11330 9; 16/1133

-T-T

H1, H 1 H 1 , H 1 BruttoformelGross formula

Ref. 2927Ref. 2927

Bor· Gef.Boron · Gef.

# N JC N# N JC N

63. Hf-JH -C CH63. Hf-JH -C CH

-CH.,-CH., -H -H-H -H

11,2 11,611.2 11.6

65. -CH,65. -CH,

-CH,-CH,

-C2H5 -H -H C14H11O3N3S 14,0 13,5 -C 2 H 5 -H-HC 14 H 11 O 3 N 3 S 14.0 13.5

-H -H C9H12O3N2 14,3 14,7 -H -H C,„H,q0-Np 11,8 11,2-H-HC 9 H 12 O 3 N 2 14.3 14.7 -H-HC, "H, q 0 -N p 11.8 11.2

-CH2-CH2-CN-CH 2 -CH 2 -CN

-CH2-CH2-OH-CH 2 -CH 2 -OH

-CHg-CHg-OCH--CHg-CHg-OCH- -H-HC-H-HC

19,0 19,519.0 19.5

-H -H C9H12O4N2 13,3 13,9 -H -H C10H14O4N2 12,4 13,0-H-HC 9 H 12 O 4 N 2 13.3 13.9 -H-HC 10 H 14 O 4 N 2 12.4 13.0

CH, 70. -CH3 -CHgCHgCH2-N^ ·> -H-H C12H19O3N3 16,6 16,2CH, 70. -CH 3 -CHgCHgCH 2 -N ^ •> -HH C 12 H 19 O 3 N 3 16.6 16.2

71. -CH_ -CH2-CH2-IiH-^H3 -H -H71. -CH_ -CH 2 -CH 2 -IiH- ^ H 3 -H -H

72. -CH3 72. -CH 3

73. -CH,73. -CH,

-NH-CH.-NH-CH. -H -H CJLxOJS1 -H -H CJL x OJS 1

7H9( 7 H 9 (

18,7 18,518.7 18.5

22,9 22,522.9 22.5

-H -H CgH11O3K3 21,4 21,0-H -H CgH 11 O 3 K 3 21.4 21.0

74. -CH,74. -CH,

75. -CH3 75. -CH 3

-NH-CO-CH,-NH-CO-CH, -H -H C9H11O4N3 18,7 18,5-H-HC 9 H 11 O 4 N 3 18.7 18.5 -H -H C11H16O3N2 12,5 12,0-H-HC 11 H 16 O 3 N 2 12.5 12.0

76. -CH,76. -CH,

77. -CH,77. -CH,

-CHsCH.-CHsCH.

-H -H C9H10O3N2 14,4 14,0-H-HC 9 H 10 O 3 N 2 14.4 14.0 -H -H C13H18O3N2 11,2 11,6-H-HC 13 H 18 O 3 N 2 11.2 11.6

309816/1133309816/1133

Ref. 2927Ref. 2927

No.No.

Brutto- Bar« Gef.Gross bar «Gef.

formelformula

78. -CH3 78. -CH 3

79. -CH3 80» -CH,79. -CH 3 80 »-CH,

-oh/-Oh/

-H -H -H-H -H -H

-H C14H14O3N2 10,9 10,5 -H C13H12O3N2 11,5 11,0 -H C11H10O4N2 12,0 12,5-HC 14 H 14 O 3 N 2 10.9 10.5 -HC 13 H 12 O 3 N 2 11.5 11.0 -HC 11 H 10 O 4 N 2 12.0 12.5

81.-CH2-CH2-CH2-NH2 _H _H _H 82.-CH2-CH2-CH2-CN -H -H -H81.-CH 2 -CH 2 -CH 2 -NH 2 _ H _ H _ H 82.-CH 2 -CH 2 -CH 2 -CN -H -H -H

I9, 9 20,3 19,0 19,4I 9, 9 20.3 19.0 19.4

83 .-CH2CH2CH2-OCH3 83.-CH 2 CH 2 CH 2 -OCH 3

. -CH2-NH-CH3 . -CH 2 -NH-CH 3

-H -H-H -H

-H C10H14O4N2 12,4 12,8-HC 10 H 14 O 4 N 2 12.4 12.8

-H -H -H C8H11O3N3 21,3 21,6-H -H-HC 8 H 11 O 3 N 3 21.3 21.6

-H -H-H -H

20,9 21,320.9 21.3

-CH3 -CH 3

-CH- -CH--CH- -CH-

-H -H -CH3 C8H10O3N2 15,4 15,0-H -H -CH 3 C 8 H 10 O 3 N 2 15.4 15.0

-H -CH3 -CH3 C9H13O3N2 14,3 14,0-H -CH 3 -CH 3 C 9 H 13 O 3 N 2 14.3 14.0

-CH3 -CH3 -CH3 C10H14O3N2 13,3 13,6-CH 3 -CH 3 -CH 3 C 10 H 14 O 3 N 2 13.3 13.6

-CH3 -C4H9(Ii) -H -C4H9(H) C15H24O3N2 10,0 10,5-CH 3 -C 4 H 9 (Ii) -H -C 4 H 9 (H) C 15 H 24 O 3 N 2 10.0 10.5

-CH3 -H -CH2CH2-OH -CHgCHgOH-CH 3 -H -CH 2 CH 2 -OH -CHgCHgOH

10,9 10,410.9 10.4

-CH3 -H -H -CH^CH2CHgOCH3 C11H16O4N2 11,7 11,5 -CH3 -CHgCH2OCH3 _H -CHgCHgOCH3 C13H20O5N2 10,1 10,5-CH 3 -H -H -CH 2 CH ^ CHgOCH 3 C 11 H 16 O 4 N 2 11.7 11.5 3 -CHgCH -CH 2 OCH 3 H _ -CHgCHgOCH 3 C 13 H 20 O 5 N 2 10 , 1 10.5

-CH3 -H-CH 3 -H

-H-H

C13H18°3N2 C 13 H 18 ° 3 N 2

3098 16/11333098 16/1133

Ref. 2927Ref. 2927

No. XNo. X

BruttoformelGross formula

Ber. Gef.Ber. Found

% N % N % N % N

. -CH3 -CH3 -H. -CH 3 -CH 3 -H

95. -CH3 -H -H95. -CH 3 -H -H

f~\ ci3Hi2°3N2 f ~ \ c i3 H i2 ° 3 N 2

O3N2 10,3 10,6 1>5 13L'8 O 3 N 2 10.3 10.6 1> 5 13L ' 8

96. -CH3 -H -CH2-CH2-O-CH2-CH2-11,8 12,296. -CH 3 -H -CH 2 -CH 2 -O-CH 2 -CH 2 -11.8 12.2

97. -CH3 -CH3 -CH2-CH2-97. -CH 3 -CH 3 -CH 2 -CH 2 - C10H12°3N2 13'5 C 10 H 12 ° 3 N 2 13 ' 5

98. -CH3 -C2H5 98. -CH 3 -C 2 H 5

-H -C-H -C

2H5 C11H16°3N2 12»5 2 H 5 C 11 H 16 ° 3 N 2 12 » 5

99. -CH3 -H99. -CH 3 -H

-H -C2H5 C9H12O3N2 14,3-H -C 2 H 5 C 9 H 12 O 3 N 2 14.3

100.100.

-H-H

-H-H

-C2H5 13,3 13,5-C 2 H 5 13.3 13.5

101. -C2H5 -CH3 101. -C 2 H 5 -CH 3

H -CHgCH2-OHH -CHgCH 2 -OH

11,7 12,111.7 12.1

H -C2H5 C14H22O3N2 10,5 10,3H -C 2 H 5 C 14 H 22 O 3 N 2 10.5 10.3

103. -CH3 103. -CH 3

-H 11,5 20,0-H 11.5 20.0

104. -CH,104. -CH,

C19H28°3N2 C 19 H 28 ° 3 N 2

309816/1133309816/1133

Claims (1)

- 15 - Ref. 2927- 15 - Ref. 2927 PatentansprücheClaims Verfahren zur Herstellung von 6-Hydroxy-2-pyridon-3-carbonsäureamiden der allgemeinen FormelProcess for the preparation of 6-hydroxy-2-pyridone-3-carboxamides of the general formula in der X Wasserstoff, eine Cyan-, eine Alkoxy-, eine gegebenenfalls verzweigte und/oder substituierte Alkyl-, gegebenenfalls verzweigte und/oder substituierte Alkenyl-, gegebenenfalls substituierte Cycloalkyl-, Aralkyl-, Arylgruppe oder einen heterocyclischen Rest,in which X is hydrogen, cyano, alkoxy, optionally branched and / or substituted alkyl, optionally branched and / or substituted alkenyl, optionally substituted cycloalkyl, aralkyl, aryl group or a heterocyclic radical, Y Wasserstoff, eine gegebenenfalls substituierte Aaino-, gegebenenfalls verzweigte ' und/oder substituierte Alkyl-, gegebenenfalls verzweigte und/oder substituierte Alkenyl-, gegebenenfalls substituierte Cycloalkyl-, Aralkyl- oder Arylgruppe oder einen heterocyclischen Rest,Y is hydrogen, an optionally substituted Aaino-, optionally branched ' and / or substituted alkyl, optionally branched and / or substituted Alkenyl, optionally substituted cycloalkyl, aralkyl or aryl group or a heterocyclic radical, und/oder R2 Wasserstoff, eine Alkyl-, Hydroxyalkyl-, Alkoxyalkyl-, Cycloalkyl-, Aralkyl- oder Arylgruppe, wobei die Alkylreste R1 und R2 auch direkt oder Über ein Heteroatom verbunden sein könnenand / or R 2 is hydrogen, an alkyl, hydroxyalkyl, alkoxyalkyl, cycloalkyl, aralkyl or aryl group, where the alkyl radicals R 1 and R 2 can also be connected directly or via a heteroatom 309816/1133309816/1133 - 3 6 - ' lief. 2927- 3 6 - 'ran. 2927 bedeuten, dadurch gekeiitizeiclinet, daß man eine Verbindung der allgemeinen Formel IImean, thereby gekeiitizeiclinet that one compound of the general formula II ZO - CO - CH2 - CO - X IIZO - CO - CH 2 - CO - X II worin X die bereits angegebene Bedeutung besitzt und Z einen Alkylrest bedeutet, mit einer Verbindung der allgemeinen Forme] IIIwherein X has the meaning already given and Z is an alkyl radical, with a compound the general form] III HIN - CO - CII2 - CO - Nn'" J j:[J HIN - CO - CII 2 - CO - N n '" J j: [J Xr2 Xr 2 kondensiert, oder daß man eine Verbindung der allgemeinen Formel TVcondensed, or that a compound of the general formula TV HYN - CO - CH2 - CO - X IV mit einer Verbindung der allgemeinen Formel VHYN - CO - CH 2 - CO - X IV with a compound of the general formula V ZO ~ CO - CII0 - CO - NZO ~ CO - CII 0 - CO - N R2 R 2 kondensiert, wobei X, Y, IL, Ii2 und Z die bereits f angegebenen Bedeutungen besitzen,condensed, where X, Y, IL, Ii 2 and Z have the meanings already given for f, 2. Verfahren nach Anspruch 1, dadurch gekennzeichnet, daß die Kondensation in einem organischen Lösungsmittel durchgeführt wird.2. The method according to claim 1, characterized in that the condensation in an organic solvent is carried out. 3, Verfahren.nach den Anspruchen 3 biß 2, dadurch gekennzeichnet, daß die Kondensatj on in einem niederen Alkohol durchgeführt wird.3, method according to claims 3 to 2, characterized in that that the condensation in a lower Alcohol is carried out. < Π :1 : J < Π: 1: J - 17 - Ref. 2927- 17 - Ref. 2927 k. Verfahren nach den Ansprüchen 1 bis 3t dadurch gekennzeichnet, daß die Kondensation bei Temperaturen von O bis 10O0C durchgeführt wird, k. Process according to claims 1 to 3 t characterized in that the condensation at temperatures of from O to 10O 0 C is performed, 5. Verfahren nach den Ansprüchen 1 bis 4, dadurch gekennzeichnet, daß die Kondensation in Gegenwart eines alkalischen Kondensationsmittels durchgeführt wird.5. Process according to claims 1 to 4, characterized in that that the condensation is carried out in the presence of an alkaline condensing agent will. 6. Verfahren nach den Ansprüchen 1 bis 5» dadurch gekennzeichnet, daß die Kondensation in Gegenwart von Natrium— oder Kaliumalkoholat durchgeführt wird.6. Process according to claims 1 to 5 »characterized in that the condensation in the presence of Sodium or potassium alcoholate is carried out. 7. Verfahren nach tion Ansprüchen 1 bis 6, dadurch gekennzeichnet, daß X einen Alkylrest, Y Wasserstoff, einen Alkyl- oder Phenylrest, It. Wasserstoff und R_ Wasserstoff oder einen Alkylrest bedeuten, wobei die Alkylreste 1 bis 4 Kohlenstoffatome besitzen.7. The method according to claims 1 to 6, characterized in that that X is an alkyl radical, Y is hydrogen, an alkyl or phenyl radical, It. Hydrogen and R_ denotes hydrogen or an alkyl radical, the alkyl radicals having 1 to 4 carbon atoms. 8. Verfahren nach Anspruch 7, dadurch gekennzeichnet, daß die Alkylreste 1 oder 2 Kohlenstoffatome besitzen. 8. The method according to claim 7, characterized in that the alkyl radicals have 1 or 2 carbon atoms. 3 C 2 8 1 S / : 1 3 33 C 2 8 1 S /: 1 3 3
DE19712150772 1971-10-12 1971-10-12 METHOD FOR PREPARING 6-HYDROXY-2-PYRIDONE-3-CARBONIC ACID AMIDE COMPOUNDS Pending DE2150772A1 (en)

Priority Applications (5)

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DE19712150772 DE2150772A1 (en) 1971-10-12 1971-10-12 METHOD FOR PREPARING 6-HYDROXY-2-PYRIDONE-3-CARBONIC ACID AMIDE COMPOUNDS
JP10121572A JPS4844263A (en) 1971-10-12 1972-10-11
GB4687772A GB1373314A (en) 1971-10-12 1972-10-11 Process for the preparation of 6-hydroxy-2-pyridone-3-carbonic acid amides
FR7235922A FR2156231B1 (en) 1971-10-12 1972-10-11
CH1490172A CH568289A5 (en) 1971-10-12 1972-10-12

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EP0628547A1 (en) * 1993-06-14 1994-12-14 BASF Aktiengesellschaft Process for the preparation of N-aminopyridones

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AU6049199A (en) 1998-09-16 2000-04-03 Dow Agrosciences Llc 2-methoxyimino-2-(pyridinyloxymethyl)phenyl acetamides with (derivatised) hydroxyalkyl derivatives on the pyridine ring
ES2546386T3 (en) * 1999-07-20 2015-09-23 Dow Agrosciences, Llc Fungicide heterocyclic aromatic amides and their compositions, methods of use and preparation
EP1516874B1 (en) * 1999-07-20 2015-08-19 Dow AgroSciences LLC Fungicidal heterocyclic aromatic amides and their compositions, methods of use and preparation
US7732616B2 (en) 2003-11-19 2010-06-08 Array Biopharma Inc. Dihydropyridine and dihydropyridazine derivatives as inhibitors of MEK and methods of use thereof
DE602004031037D1 (en) * 2003-11-19 2011-02-24 Array Biopharma Inc HETEROCYCLIC INHIBITORS OF MEK
US7517994B2 (en) 2003-11-19 2009-04-14 Array Biopharma Inc. Heterocyclic inhibitors of MEK and methods of use thereof
MY149960A (en) 2005-05-18 2013-11-15 Array Biopharma Inc 4-(phenylamino)-6-oxo-1,6-dihydropyridazine-3-carboxamide derivatives as mek inhibitors for the treatment of hyperproliferative diseases
JP5020542B2 (en) 2006-05-19 2012-09-05 キヤノン株式会社 Novel coloring compound and ink containing the coloring compound

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GB1263268A (en) * 1968-12-11 1972-02-09 Ici Ltd 0-aminoalkyl-pyridin-2-ones

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0628547A1 (en) * 1993-06-14 1994-12-14 BASF Aktiengesellschaft Process for the preparation of N-aminopyridones
US5466812A (en) * 1993-06-14 1995-11-14 Basf Aktiengesellschaft Preparation of N-aminopyridones

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GB1373314A (en) 1974-11-06
CH568289A5 (en) 1975-10-31
FR2156231A1 (en) 1973-05-25
JPS4844263A (en) 1973-06-26

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