DE2701659A1 - 2-Hydroxy-pyridone and 1-hydroxy-pyrido:benzimidazole amide derivs. - prepd. from keto-acetate and malonamide or acetamide cpd., for dyestuff prodn. - Google Patents

2-Hydroxy-pyridone and 1-hydroxy-pyrido:benzimidazole amide derivs. - prepd. from keto-acetate and malonamide or acetamide cpd., for dyestuff prodn.

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DE2701659A1
DE2701659A1 DE19772701659 DE2701659A DE2701659A1 DE 2701659 A1 DE2701659 A1 DE 2701659A1 DE 19772701659 DE19772701659 DE 19772701659 DE 2701659 A DE2701659 A DE 2701659A DE 2701659 A1 DE2701659 A1 DE 2701659A1
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Ernst Dipl Chem Dr Schefczik
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BASF SE
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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
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D471/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00
    • C07D471/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00 in which the condensed system contains two hetero rings
    • C07D471/04—Ortho-condensed systems
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
    • C09B29/00—Monoazo dyes prepared by diazotising and coupling
    • C09B29/34—Monoazo dyes prepared by diazotising and coupling from other coupling components
    • C09B29/36—Monoazo dyes prepared by diazotising and coupling from other coupling components from heterocyclic compounds
    • C09B29/3604—Monoazo dyes prepared by diazotising and coupling from other coupling components from heterocyclic compounds containing only a nitrogen as heteroatom
    • C09B29/3617—Monoazo dyes prepared by diazotising and coupling from other coupling components from heterocyclic compounds containing only a nitrogen as heteroatom containing a six-membered heterocyclic with only one nitrogen as heteroatom
    • C09B29/3621—Monoazo dyes prepared by diazotising and coupling from other coupling components from heterocyclic compounds containing only a nitrogen as heteroatom containing a six-membered heterocyclic with only one nitrogen as heteroatom from a pyridine ring
    • C09B29/3626—Monoazo dyes prepared by diazotising and coupling from other coupling components from heterocyclic compounds containing only a nitrogen as heteroatom containing a six-membered heterocyclic with only one nitrogen as heteroatom from a pyridine ring from a pyridine ring containing one or more hydroxyl groups (or = O)
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
    • C09B29/00—Monoazo dyes prepared by diazotising and coupling
    • C09B29/34—Monoazo dyes prepared by diazotising and coupling from other coupling components
    • C09B29/36—Monoazo dyes prepared by diazotising and coupling from other coupling components from heterocyclic compounds
    • C09B29/3604—Monoazo dyes prepared by diazotising and coupling from other coupling components from heterocyclic compounds containing only a nitrogen as heteroatom
    • C09B29/3647—Monoazo dyes prepared by diazotising and coupling from other coupling components from heterocyclic compounds containing only a nitrogen as heteroatom containing a five-membered ring with two nitrogen atoms as heteroatoms

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

Abstract

New pyridine derivs. are of formula (I) In (I) r is H or 1-4C alkyl. R1 is a (cyclo)aliphatic, araliphatic or aromatic gp. X is O or R' and X together are a gp. of formula (II); Y iH, Me, Et, MeO, EtO, Cl, Br, hydroxysulphonyl, carboxyl, 1-4C alkoxycarbonyl or carbamoyl. R and R1 pref. are 1-8C alkyl, beta-hydroxy-or -(m)-ethoxy-ethyl or -propyl, beta-cyanoethyl or phenylethyl. (I) are used for the prodn. of dyestuffs. They are valuable coupling components for the prodn. of azo dyestuffs and can also be used as CH-acid cpds., e.g. for condensn. reactions leading to dyestuffs.

Description

Verbindungen der PyridinreiheCompounds of the pyridine series

Die Erfindung betrifft Verbindungen der allgemeinen Formel I in der R Wasserstoff oder C1-bis C4-Alkyl, R einen aliphatischen, cycloaliphatischen, araliphatischen oder arosatischen Rost, x Sauerstoff oder R¹ und X zusammen einen Rest der Formel bedeuten, wobei Y Wasserstoff, Methyl, Äthyl, Methoxy, Äthoxy, Chlor, Brom, Hydroxysulfonyl, Carboxyl, C1- bis C4-Ilkoxycarbonyl oder C rbasoyl ist.The invention relates to compounds of the general formula I. in which R is hydrogen or C1 to C4 alkyl, R is an aliphatic, cycloaliphatic, araliphatic or arosatic rust, x is oxygen or R¹ and X together is a radical of the formula mean, where Y is hydrogen, methyl, ethyl, methoxy, ethoxy, chlorine, bromine, hydroxysulfonyl, carboxyl, C1- to C4-ilkoxycarbonyl or C rbasoyl.

Alkylreste R sind zoBo Äthyl, Propyl oder Butyl und vorzugsweise Methyl.Alkyl radicals R are eg ethyl, propyl or butyl and preferably methyl.

Als Reste R¹ sind beispielaweise gegebenenfalls durch Hydroxy, C1- bis C8-Alkoxy, Cyan oder Phenoxy substituiertes C1 - bis C8-Alkyl, Cyclohexyl, Benzyl, Phenyläthyl, Phenylpropyl, Phenylbutyl oder gegebenenfalls durch Methyl, Äthyl, Methoxy, Äthoxy, Chlor oder Brom substituiertes Phenyl zu nennen, Einzelne Reste sind neben den bereits genannten z.B. Methyl, Äthyl, Propyl, Isopropyl, Butyl, eek. Butyl, tert. Butyl, 2-Äthylhexyl, 2-Hydroxyäthyl, 2-Methoxyäthyl, 2-Cyanäthyl, 2-Phenoxyäthyl, 3-Hydroxypropyl, 3-Äthoxypropyl, 3-butoxypropyl, 3-(2-Äthylhexoxy)propyl, 5-Cyanphenyl, 3-(4-Hydroxybutoxy)propyl.The radicals R¹ are, for example, optionally substituted by hydroxy, C1- C1- to C8-alkyl, cyclohexyl, benzyl substituted up to C8-alkoxy, cyano or phenoxy, Phenylethyl, phenylpropyl, phenylbutyl or optionally methyl, ethyl, Methoxy, ethoxy, chlorine or bromine substituted phenyl to be mentioned, individual radicals are in addition to those already mentioned e.g. methyl, ethyl, propyl, isopropyl, butyl, eek. Butyl, tert. Butyl, 2-ethylhexyl, 2-hydroxyethyl, 2-methoxyethyl, 2-cyanoethyl, 2-phenoxyethyl, 3-hydroxypropyl, 3-ethoxypropyl, 3-butoxypropyl, 3- (2-ethylhexoxy) propyl, 5-cyanophenyl, 3- (4-hydroxybutoxy) propyl.

Alkoxycarbonylreste Y sind z.B. Butoxycarbonyl, Propoxycarbonyl und insbesondere Methoxy- und Äthoxycarbonyl.Alkoxycarbonyl radicals Y are, for example, butoxycarbonyl, propoxycarbonyl and especially methoxy and ethoxycarbonyl.

Zur Herstellung der Verbindungen der Formel I kann man Verbindungen der Formel II H-CO-CE2-COOB II, wobei B C1- bis C4-Alkyl ist, mit Verbindungen der Formel III umsetzen, R, R¹ und Y haben dabei die angegebenen Bedeutungen, Die Reaktionsbedingungen können analog zu denen gewählt werden, die zur Herstellung von beispielsweise 2-Hydroxy-3-cyan-6-pyridenen dienen.To prepare the compounds of the formula I, compounds of the formula II H-CO-CE2-COOB II, where B is C1- to C4-alkyl, can be used with compounds of the formula III react, R, R¹ and Y have the meanings given, The reaction conditions can be chosen analogously to those used for the preparation of, for example, 2-hydroxy-3-cyano-6-pyridenes.

Von besondererf Bedeutung sind Verbindungen der Formel Ia in der R² C1- bis C8-Alkyl, B-Hydroxyäthyl oder -propyl, B-Cyanäthyl, B-Methotyäthyl oder -propyl, ß-Äthoyxäthyl oder -propyl oder Phenyläthyl, X Sauerstoff und X und R2 zusammen den Rest bedeuten.Compounds of the formula Ia are of particular importance in R² C1- to C8-alkyl, B-hydroxyethyl or -propyl, B-cyanoethyl, B-methotyethyl or -propyl, ß-ethoxyethyl or -propyl or phenylethyl, X oxygen and X and R2 together the rest mean.

Bevorsugte Reste R2 sind Methyl, Äthyl, 2-Eydroxyäthyl, 2-Cyanäthyl und 2-Phenyläthyl.Prevented residues R2 are methyl, ethyl, 2-hydroxyethyl, 2-cyanoethyl and 2-phenylethyl.

Die Verbindungen der Formel I sind wertvolle Kupplungskomponenten zur Herstellung von Azofarbstoffen, ferner können sie als CH-acide Verbindungen für z.B. zu Farbetoffen führenden Kondensationsreaktionen verwendet werden.The compounds of the formula I are valuable coupling components for the production of azo dyes, they can also be used as CH-acidic compounds be used for condensation reactions leading to dyes, for example.

In den folgenden Beispielen beziehen sich Angaben über Teile und Prozente, sofern nicht anders vermerkt, auf das Gewicht.In the following examples, parts and percentages relate to unless otherwise noted, by weight.

Beispiel 1 65 Teile Natriummethylat werden in 500 Raumteilen Glykolmonomethyläther gelöst. Dazu gibt man 130 Teile Acetessigsäureäthylester und 310 Teile Malonsäure-bis-phenyläthylamid. Das Gemisch wird 10 Stunden gekocht, wobei man über einen absteigenden SUhler Äthanol abdem destillieren läßt. Nach Erkalten rührt man in kalte 5 %ige Salzsäure ein und saugt das ausgefallene Produkt ab. Man wäscht mit Wasser chloridfrei und trocknet bei 60 °C im Vakuum. Ausbeute 241 Teile 1-Phenyläthyl-2-hydroxy-4-methylpyrid-6-on-4-carbonyäurephenyläthylamid. Eis aus Äthanol umkristallisierte Probe zeigt einen Schmelzpunkt von 147 - 148 OC und folgende Analysenwerte: C23H24N2O3 (376) ber. C 73,4 H 6,4 N 7,4 0 12,7 gef. 73,1 6,3 7,7 13,2 Beispiel 2 In ein Gemisch aus 75 Teilen lmeisensäureäthylester und 120 Teilen Essigsäureäthylester werden unter Kühlen bei -10 bis 0 OC 72 Teile Natriummethylat eingetragen. Man läßt über Nacht bei Raumtemperatur stehen, löst dann den farblosen Kristallbrei durch Übergießen mit 750 Beurteilen absolutem Äthanol und trägt 130 Teile Malonsäurebis-iethylaiid ein. Nun kocht man 8 Stunden unter Rückfluß, wobei da Reaktionsgemisch allmählich zu einem Kristallbrei eretarrt.Example 1 65 parts of sodium methylate are used in 500 parts by volume of glycol monomethyl ether solved. 130 parts of ethyl acetoacetate and 310 parts of bis-phenylethyl amide are added. The mixture is boiled for 10 hours, with ethanol being poured over a descending liquid from then can be distilled. After cooling, the mixture is stirred into cold 5% hydrochloric acid and sucks off the failed product. It is washed free of chloride with water and dried at 60 ° C in a vacuum. Yield 241 parts of 1-phenylethyl-2-hydroxy-4-methylpyrid-6-one-4-carbonyäurephenyläthylamid. A sample recrystallized from ethanol has a melting point of 147-148 ° C and the following analytical values: C23H24N2O3 (376) calcd. C 73.4 H 6.4 N 7.4 0 12.7 found. 73.1 6.3 7.7 13.2 Example 2 In a mixture of 75 parts of ethyl formate and 120 parts of ethyl acetate are 72 parts with cooling at -10 to 0 ° C Sodium methylate entered. It is left to stand overnight at room temperature and dissolves then the colorless crystal pulp by pouring 750 absolute ethanol over it and enters 130 parts of malonic acid bis-ethylidide. Now cook under for 8 hours Reflux, the reaction mixture gradually solidifying to form a slurry of crystals.

Dann gibt man überschüssige 10 ziege Salzsäure zu und destilliert Äthanol/Wasser ab bis die Innentemperatur 100 °C erreicht. Aus der klaren Lösung scheiden sich beim Erkalten farblose Kristalle aus, die abgesaugt und getrocknet werden. Ausbeute 123 Teile 1-Methyl-2-hydroxypyrid-6-on-3-carbonsäuremethylamid von Schmelzpunkt 206 - 208 °C.Then excess goat hydrochloric acid is added and the mixture is distilled Ethanol / water from until the internal temperature reaches 100 ° C. From the clear solution Colorless crystals separate on cooling, which are sucked off and dried will. Yield 123 parts of 1-methyl-2-hydroxypyrid-6-one-3-carboxylic acid methylamide of melting point 206 - 208 ° C.

Analyse: CBE10N203 (182) ber. C 52,8 H 5,5 N 15,4 0 26,4 gef. 52,8 5,5 15,5 26,4 Nach den in den Beispielen 1 und 2 geschilderten Verfahren wurden die folgenden Verbindungen der Formel I erhalten: Bep. R R1 rp 3 H -CH2CH3 167-168 0C (Äthanol) 4 H -CH2CH20H 163-164 0C (Wasser) 5 H -CH2CH2CH3 149-150 OC 6 H -CH2CH2CN 172-173 OC 7 H -CH2CH2CH20CH3 127-128 0C (Wasser) 8 H CH2CH2CH2CH3 87 - 89 Oc (Methanol) 9 H CH2CHC2H5 wachsartig CqIg 10 H 6 156-157 OC (Xylol) 11 H -CH2CH2C6H5 122-123 °C (Xylol) 12 H -C6H5 236 0C (Essigsäure) 13 -CH3 -CH3 132-133 0C (Äthanol) 14 -CH3 -CH2CH3 97-98 0C (Methanol) 15 -CH2CH2CH2CH3 -CH2CH3 wachsartig Beispiel 16 In 750 Rausteile Äthylenglykolmonoäthyläther wurden 60 Teile Natriummethylat, 130 Teile Acetessigsäureäthylester und 189 Teile Benzimidazolyl-2-acet-N-methylamid eingetragen. Man kocht 6 Stunden am absteigenden Kühler unter Abdestillieren des bei der Kondensation entstehenden Ätnanols, setzt 250 Raumteile Wasser zu und filtriert.Analysis: CBE10N203 (182) calcd. C 52.8 H 5.5 N 15.4 0 26.4 found. 52.8 5.5 15.5 26.4 The following compounds of the formula I were obtained by the processes outlined in Examples 1 and 2: Beep R R1 rp 3 H -CH2CH3 167-168 0C (ethanol) 4 H -CH2CH20H 163-164 0C (water) 5 H -CH2CH2CH3 149-150 OC 6 H -CH2CH2CN 172-173 OC 7 H -CH2CH2CH20CH3 127-128 0C (water) 8 H CH2CH2CH2CH3 87-89 Oc (methanol) 9 H CH2CHC2H5 waxy CqIg 10 H 6 156-157 OC (xylene) 11 H -CH2CH2C6H5 122-123 ° C (xylene) 12 H -C6H5 236 0C (acetic acid) 13 -CH3 -CH3 132-133 0C (ethanol) 14 -CH3 -CH2CH3 97-98 0C (methanol) 15 -CH2CH2CH2CH3 -CH2CH3 waxy EXAMPLE 16 60 parts of sodium methylate, 130 parts of ethyl acetoacetate and 189 parts of benzimidazolyl-2-acet-N-methylamide were introduced into 750 parts of ethylene glycol monoethyl ether. The mixture is boiled for 6 hours on the descending cooler while distilling off the ethanol formed during the condensation, 250 parts by volume of water are added and the mixture is filtered.

Das Filtrat wird in überschüssige 10 %ige Essigsäure eingerührt und die Suspension zur besseren Kristallisation des Reaktionsprodukte dem aufgekocht. Nach Absaugen, Waschen mit Wasser und Trocknen erhält man 195 Teile einer Vergbindung der Formel I (R # R¹ = CH3, Y = H).The filtrate is stirred into excess 10% acetic acid and the suspension is boiled for better crystallization of the reaction products. After filtering off with suction, washing with water and drying, 195 parts of a compound are obtained of formula I (R # R¹ = CH3, Y = H).

Eine aus Dimethylformamid umkristallisierte Probe schmilzt bei 348 °C unter Zersetzung und zeigt folgende Analysenwerte: C14H13N3O2 (255) ber. C 65,9 R 5,1 N 16,5 0 12,5 gef. 65,5 5,3 16,8 12,8 Beispiel 17 In ein Gemisch aus 80 Teilen imeisensäureäthylester und 140 Teilen Essigsäureäthylester werden unter Kühlen bei -20 bis 9 °C 77 Teile Natriummethylat eingetragen. Nach dem Stehenlassen über Nacht wird der farblose Salzbrei von Natrium-Formylessigester durch Zugabe von 400 Raumteilen Äthylenglykolmonomethyläther in Lösung gebracht und die Lösung mit 189 Teilen Benzimidazolyl-2-acet-N-methylamid versetzt. Man kocht 4 Stunden unter Rückfluß, setzt 600 Baumteile Wasser zu und säuert mit conc. Salzsäure an. Das Reaktionsgemisch wird 1/2 Stunde gekocht, mit Natriumacetat bis zur neutralen Reaktion versetzt und abgesaugt. Nach dem Waschen mit warmem Wasser und Trocknen erhält man 208 Teile einer Verbindung der Formel I ( =H, R1 = CH3, Y = H). Der Schmelzpunkt einer aus Dimethylformamid umkristallisierten Probe liegt bei 321 OC (unter Zersetzung).A sample recrystallized from dimethylformamide melts at 348 ° C with decomposition and shows the following analysis values: C14H13N3O2 (255) calc. C 65.9 R 5.1 N 16.5 0 12.5 found. 65.5 5.3 16.8 12.8 Example 17 In a Mixture of 80 parts of ethyl acetate and 140 parts of ethyl acetate 77 parts of sodium methylate are introduced with cooling at -20 to 9 ° C. To if left to stand overnight, the colorless salt paste becomes sodium formyl acetic ester brought into solution by adding 400 parts by volume of ethylene glycol monomethyl ether and 189 parts of benzimidazolyl-2-acet-N-methylamide are added to the solution. You cook 4 hours under reflux, 600 parts of trees are added to water and acidified with conc. hydrochloric acid at. The reaction mixture is boiled for 1/2 hour, with sodium acetate until neutral Reaction added and sucked off. After washing with warm water and drying 208 parts of a compound of the formula I (= H, R1 = CH3, Y = H) are obtained. The melting point a sample recrystallized from dimethylformamide is at 321 ° C. (with decomposition).

Analyse: C13z11N302 (241) ber. C 64,8 H 4,6 N 17,4 0 13,3 gef. 64,5 4,9 17,3 13,7 Analog den Beispielen 16 und 17 wurden die folgenden Verbindungen der Formel erhalten 1 Bsp. R R1 y Schmelzpunkt 18 H -CH2CH3 H 318 OC Z (Diiethylforaaiid) 19 H -CH2CH2CH3 H 264-265 OC (Nitrobenzol) 20 H CHCH3 H 270-271 OC (Cyclohexanol) CH3 21 H -CH2CH2CH2OC2H5 H 187-188 OC (Butanol) 22 R -CH2CH2C6H5 H 222-223 °C (Pentanol) 23 H -C6H5 H 338 0C Z (Di.ethylforaiid) 24 -Cfi3 -CH2CH2CH2Cli3 H 195-196 0C (Pentanol) 25 H -CH3 Cl a350 0C 26 H -CH2CH20CH3 -CH3 * 27 H -CH2CH2CH3 -OCH3 * 28 H -CH2CH2CH20C4Hg -OC2H5 * 29 H -CH2CH2OC6H5 OC2H5 * 30 H -CH2CH3 -COOC2H5 * 31 H -CH3 -S03H >350 Oc 32 H Ihr -S03H 2350 °C 33 -CH2CH3 -CH3 -S03H >350 OC *) kein scharfer Schmelzpunkt, da Isomerengemisch in Bezug auf YAnalysis: C13z11N302 (241) calcd. C 64.8 H 4.6 N 17.4 0 13.3 found. 64.5 4.9 17.3 13.7 The following compounds of the formula were analogous to Examples 16 and 17 get 1 Ex. R R1 y melting point 18 H -CH2CH3 H 318 OC Z (Diiethylforaaiid) 19 H -CH2CH2CH3 H 264-265 OC (nitrobenzene) 20 H CHCH3 H 270-271 OC (cyclohexanol) CH3 21 H -CH2CH2CH2OC2H5 H 187-188 OC (butanol) 22 R -CH2CH2C6H5 H 222-223 ° C (pentanol) 23 H -C6H5 H 338 0C Z (Di.ethylforaiid) 24 -Cfi3 -CH2CH2CH2Cli3 H 195-196 0C (pentanol) 25 H -CH3 Cl a350 0C 26 H -CH2CH20CH3 -CH3 * 27 H -CH2CH2CH3 -OCH3 * 28 H -CH2CH2CH20C4Hg -OC2H5 * 29 H -CH2CH2OC6H5 OC2H5 * 30 H -CH2CH3 -COOC2H5 * 31 H -CH3 -S03H> 350 Oc 32 H your -S03H 2350 ° C 33 -CH2CH3 -CH3 -S03H> 350 OC *) no sharp melting point, as a mixture of isomers in relation to Y

Claims (4)

Patentansprüche 9 Verbindungen der Pyridinreihe der allgemeinen Formel in der s Wasserstoff oder C1 - bis C4-Alkyl, R¹ einen aliphatischen, cycloaliphatischen, araliphatischen oder aromatischen Rest, X Sauerstoff oder R¹ und X zusammen einen Rest der Formel bedeuten, wobei Y Wasserstoff, Methyl, Äthyl, Methoxy, Äthoxy, Chlor, Brom, Hydroxysulfonyl, Carboxyl, C1-bis C4-Alkoxycarbonyl oder Carbamoyl ist.Claims 9 compounds of the pyridine series of the general formula in which s is hydrogen or C1- to C4-alkyl, R¹ is an aliphatic, cycloaliphatic, araliphatic or aromatic radical, X is oxygen or R¹ and X together is a radical of the formula mean, where Y is hydrogen, methyl, ethyl, methoxy, ethoxy, chlorine, bromine, hydroxysulfonyl, carboxyl, C1- to C4-alkoxycarbonyl or carbamoyl. 2. Verbindungen gemäß Anspruch 1 der Formel in der R2 C1- bis C8-Alkyl, R-Hydroxyäthyl oder -propyl, B-Cyanäthyl, ß-Methoxyäthyl oder -propyl, B-Athoxyäthyl oder -propyl oder Phenyläthyl, X Sauerstoff und X und R2 zusammen den Rest bedeuten.2. Compounds according to claim 1 of the formula in R2 C1- to C8-alkyl, R-hydroxyethyl or -propyl, B-cyanoethyl, ß-methoxyethyl or -propyl, B-ethoxyethyl or -propyl or phenylethyl, X oxygen and X and R2 together the remainder mean. 3. Verfahren zur Herstellung von Verbindungen gemäß Anspruch 1,. dadurch gekennzeichnet, daß man Verbindungen der Fonnel R-CO-CH2-COOB wobei B C1 - bis C4-Alkyl ist, mit Verbindungen der Formel umsetzt, R, R und Y haben dabei die für Anspruch 1 angegebenen Bedeutungen.3. A process for the preparation of compounds according to claim 1. characterized in that compounds of the formula R-CO-CH2-COOB where B is C1- to C4-alkyl, with compounds of the formula converts, R, R and Y have the meanings given for claim 1. 4. Die Verwendung der Verbindungen gemäß Anspruch 1 zur Herstellung von Farbstoffen.4. The use of the compounds according to claim 1 for the preparation of dyes.
DE19772701659 1977-01-17 1977-01-17 2-Hydroxy-pyridone and 1-hydroxy-pyrido:benzimidazole amide derivs. - prepd. from keto-acetate and malonamide or acetamide cpd., for dyestuff prodn. Withdrawn DE2701659A1 (en)

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Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2004050768A2 (en) * 2002-12-05 2004-06-17 Ciba Specialty Chemicals Holding Inc. Benzimidazole-pyridone-based azo dyes

Cited By (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2004050768A2 (en) * 2002-12-05 2004-06-17 Ciba Specialty Chemicals Holding Inc. Benzimidazole-pyridone-based azo dyes
WO2004050768A3 (en) * 2002-12-05 2004-08-12 Ciba Sc Holding Ag Benzimidazole-pyridone-based azo dyes
US7217803B2 (en) 2002-12-05 2007-05-15 Ciba Specialty Chemicals Corporation Benzimidazole-pyridone-based azo dyes

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