DE3528459A1 - Difluoropyridine derivatives - Google Patents

Difluoropyridine derivatives

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Publication number
DE3528459A1
DE3528459A1 DE19853528459 DE3528459A DE3528459A1 DE 3528459 A1 DE3528459 A1 DE 3528459A1 DE 19853528459 DE19853528459 DE 19853528459 DE 3528459 A DE3528459 A DE 3528459A DE 3528459 A1 DE3528459 A1 DE 3528459A1
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DE
Germany
Prior art keywords
parts
compounds
chlorine
bromine
nitro
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.)
Withdrawn
Application number
DE19853528459
Other languages
German (de)
Inventor
Alfred Dr Hackenberger
Manfred Dr Patsch
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.)
BASF SE
Original Assignee
BASF SE
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 BASF SE filed Critical BASF SE
Priority to DE19853528459 priority Critical patent/DE3528459A1/en
Publication of DE3528459A1 publication Critical patent/DE3528459A1/en
Withdrawn legal-status Critical Current

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Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
    • C07D405/02—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings
    • C07D405/04—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings directly linked by a ring-member-to-ring-member bond
    • 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

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

Abstract

The invention relates to compounds of the general formula I <IMAGE> in which R is hydrogen or a (cyclo)aliphatic, araliphatic, aromatic or heteroaromatic radical which is optionally substituted by fluorine, chlorine, bromine, methoxy, ethoxy, nitro, C1- to C4-alkyl, methylsulphonyl, ethylsulphonyl, cyano or hydroxysulphonyl. The compounds according to the invention are suitable after linkage to dyestuffs as reactive compounds.

Description

Die Erfindung betifft Verbindungen der allgemeinen Formel I in der R Wasserstoff oder ein gegebenenfalls durch Fluor, Chlor, Brom, Methoxy, Ethoxy, Nitro, C1- bis C4-Alkyl, Methylsulfonyl, Ethylsulfonyl, Cyan oder Hydroxysulfonyl substituierter (cyclo)aliphatischer, araliphatischer, aromatischer oder heteroaromatischer Rest ist.The invention relates to compounds of general formula I. in which R is hydrogen or a (cyclo) aliphatic, araliphatic, aromatic or heteroaromatic radical which is optionally substituted by fluorine, chlorine, bromine, methoxy, ethoxy, nitro, C 1 - to C 4 -alkyl, methylsulfonyl, ethylsulfonyl, cyano or hydroxysulfonyl.

Zur Herstellung der Verbindung der Formel I kann man z. B. die entsprechenden Dichlorverbindungen mit Alkalifluoriden oder auch HF umsetzen. In den Resten R vorhandene Substituenten kann man gegebenenfalls auch noch nach dem Austausch der Chloratome nach an sich bekannten Methoden, wie Nitrierung, Chlorierung oder Sulfierung, einführen.To prepare the compound of formula I, z. B. the corresponding Implement dichloro compounds with alkali fluorides or HF. In The substituents present in the radicals R can also, if appropriate, be added after the exchange of the chlorine atoms by methods known per se, such as nitration, Introduce chlorination or sulfonation.

Einzelheiten der Herstellung der Verbindungen der Formel I können den Beispielen entnommen werden, in denen sich Angaben über Teile und Prozente, sofern nicht anders vermerkt, auf das Gewicht beziehen.Details of the preparation of the compounds of formula I can be found in the examples are taken, in which information about parts and percentages, unless otherwise noted, refer to the weight.

Die Verbindungen der Formel I eignen sich als Anker in Reaktivfarbstoffen sowie als Vorprodukte für Wirkstoffe.The compounds of formula I are suitable as anchors in reactive dyes as well as precursors for active ingredients.

Von besonderer Bedeutung sind Verbindungen der Formel I a in der der Rest A noch durch Chlor, Brom, Nitro oder Sulfo substituiert sein kann. Compounds of the formula I a are of particular importance in which the radical A can still be substituted by chlorine, bromine, nitro or sulfo.

Beispiel 1example 1

457 Teile 2,6-Dichlor-3,5-dicyan-4-phenylpyridin und 290 Teile Kaliumfluorid werden in 1219 Teilen Toluol suspendiert. Man destilliert das Toluol ab, gibt zum Rückstand 1420 Teile trockenes DMF, läßt 3 Stunden bei 70°C rühren, destilliert das DMF so weit ab, daß das heiße Reaktionsgemisch noch rührbar bleibt und gießt es auf Eiswasser. Das ausgefallene Produkt wird abgesaugt, mit Wasser gewaschen und bei Raumtemperatur getrocknet. Man erhält 384 Teile 2,6-Difluor-3,5-dicyan-4-phenylpyridin (entspricht einer Ausbeute con 95,4%).457 parts of 2,6-dichloro-3,5-dicyan-4-phenylpyridine and 290 parts of potassium fluoride are suspended in 1219 parts of toluene. The toluene is distilled from, adds 1420 parts of dry DMF to the residue, leaves at 70 ° C. for 3 hours stir, the DMF distills off until the hot reaction mixture still stirrable and pour it onto ice water. The unusual product is filtered off, washed with water and dried at room temperature. 384 parts of 2,6-difluoro-3,5-dicyan-4-phenylpyridine (corresponding to a yield of 95.4%).

Nach Umkristallisation aus Essigsäureethylester wird ein Produkt vom Schmelzpunkt 191-192°C erhalten. After recrystallization from ethyl acetate, a product of melting point 191-192 ° C. is obtained.

Beispiel 2Example 2

120 Teile 2,6-Difluor-3,5-dicyan-4-phenylpyridin werden in 1100 Teilen conc. Schwefelsäure unter Kühlung so gelöst, daß die Temperatur 10°C nicht übersteigt. Danach werden 36 Teile 98%ige Salpetersäure bei 0-10°C zugetropft und das Gemisch 1,5 Stunden bei dieser Temperatur gerührt. Man gießt auf Eiswasser, saugt das ausgefallene Produkt ab und wäscht mit Wasser säurefrei. Nach Trocknung erhält man 142 Teile 2,6-Difluor- 3,5-dicyan-4-nitrophenylpyridin.120 parts of 2,6-difluoro-3,5-dicyan-4-phenylpyridine are in 1100 parts conc. Dissolved sulfuric acid with cooling so that the temperature was 10 ° C does not exceed. Then 36 parts of 98% nitric acid at 0-10 ° C added dropwise and the mixture was stirred at this temperature for 1.5 hours.  It is poured onto ice water, the precipitated product is suctioned off and washes acid-free with water. After drying, 142 parts of 2,6-difluoro 3,5-dicyan-4-nitrophenylpyridine.

Nach Umkristallisation aus Toluol hat das Produkt einen Schmelzpunkt von 187-191°C. After recrystallization from toluene, the product has a melting point of 187-191 ° C.

Beispiel 3Example 3

50 Teile 2,6-Dichlor-3,5-dicyan-4-(2′-furyl)-pyridin und 31 Teile Kaliumfluorid werden in 130 Teilen Toluol suspendiert. Man destilliert das Toluol ab, gibt zum Rückstand 170 Teile trockenes Dimethylformamid, läßt 5 Stunden bei 70°C rühren, destilliert das Dimethylformamid so weit ab, daß das heiße Reaktionsgemisch noch rührbar bleibt und gießt auf Eiswasser. Das ausgefallene Produkt wird abgesaugt, mit Wasser gewaschen und bei Raumtemperatur getrocknet. Man erhält 44 Teile 2,6-Difluor-3,5-dicyan-4- (2′-furyl)-pyridin.50 parts of 2,6-dichloro-3,5-dicyan-4- (2'-furyl) pyridine and 31 parts of potassium fluoride are suspended in 130 parts of toluene. You distill it Toluene, 170 parts of dry dimethylformamide to the residue, 5 hours Stir at 70 ° C, the dimethylformamide distilled off so far that the hot reaction mixture remains stirrable and poured onto ice water. The precipitated product is filtered off, washed with water and at Room temperature dried. 44 parts of 2,6-difluoro-3,5-dicyan-4- are obtained. (2'-furyl) pyridine.

Nach Umkristallisation aus Essigsäureethylester wird ein Produkt vom Schmelzpunkt 160-162°C erhalten. After recrystallization from ethyl acetate, a product with a melting point of 160-162 ° C. is obtained.

Claims (3)

1. Verbindungen der allgemeinen Formel I in der R Wasserstoff oder ein gegebenenfalls durch Fluor, Chlor, Brom, Methoxy, Ethoxy, Nitro, C1- bis C4-Alkyl, Methylsulfonyl, Ethylsulfonyl, Cyan oder Hydroxysulfonyl substituierter (cyclo)aliphatischer, araliphatischer, aromatischer oder heteroaromatischer Rest ist.1. Compounds of the general formula I in which R is hydrogen or a (cyclo) aliphatic, araliphatic, aromatic or heteroaromatic radical which is optionally substituted by fluorine, chlorine, bromine, methoxy, ethoxy, nitro, C 1 - to C 4 -alkyl, methylsulfonyl, ethylsulfonyl, cyano or hydroxysulfonyl. 2. Verbindungen gemäß Anspruch 1 der Formel in der der Rest A noch durch Chlor, Brom, Nitro oder Sulfo substituiert sein kann.2. Compounds according to claim 1 of the formula in which the radical A can still be substituted by chlorine, bromine, nitro or sulfo. 3. Verwendung der Verbindungen gemäß Anspruch 1 nach der Verknüpfung mit Farbstoffen als Reaktivanker.3. Use of the compounds according to claim 1 after the link with Dyes as reactive anchors.
DE19853528459 1985-08-08 1985-08-08 Difluoropyridine derivatives Withdrawn DE3528459A1 (en)

Priority Applications (1)

Application Number Priority Date Filing Date Title
DE19853528459 DE3528459A1 (en) 1985-08-08 1985-08-08 Difluoropyridine derivatives

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
DE19853528459 DE3528459A1 (en) 1985-08-08 1985-08-08 Difluoropyridine derivatives

Publications (1)

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DE3528459A1 true DE3528459A1 (en) 1987-02-19

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Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US5081133A (en) * 1989-02-21 1992-01-14 Basf Aktiengesellschaft 2-anilinocyanopyridines having fungicidal properties

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US5081133A (en) * 1989-02-21 1992-01-14 Basf Aktiengesellschaft 2-anilinocyanopyridines having fungicidal properties

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