DK157014B - Fremgangsmaade til fremstilling af halogensubstituerede pyridiner - Google Patents
Fremgangsmaade til fremstilling af halogensubstituerede pyridiner Download PDFInfo
- Publication number
- DK157014B DK157014B DK017784A DK17784A DK157014B DK 157014 B DK157014 B DK 157014B DK 017784 A DK017784 A DK 017784A DK 17784 A DK17784 A DK 17784A DK 157014 B DK157014 B DK 157014B
- Authority
- DK
- Denmark
- Prior art keywords
- process according
- catalyst
- substituted pyridines
- organic amine
- procedure
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims description 12
- 150000003222 pyridines Chemical class 0.000 title claims description 4
- 239000003054 catalyst Substances 0.000 claims description 12
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical group [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 claims description 11
- RIOQSEWOXXDEQQ-UHFFFAOYSA-N triphenylphosphine Chemical compound C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 RIOQSEWOXXDEQQ-UHFFFAOYSA-N 0.000 claims description 8
- 150000001412 amines Chemical class 0.000 claims description 5
- 150000001875 compounds Chemical class 0.000 claims description 5
- JJWLVOIRVHMVIS-UHFFFAOYSA-N isopropylamine Chemical group CC(C)N JJWLVOIRVHMVIS-UHFFFAOYSA-N 0.000 claims description 5
- 229910052759 nickel Inorganic materials 0.000 claims description 5
- 238000002360 preparation method Methods 0.000 claims description 5
- 229910052723 transition metal Inorganic materials 0.000 claims description 4
- 150000003624 transition metals Chemical class 0.000 claims description 4
- 230000003197 catalytic effect Effects 0.000 claims description 2
- 229910052739 hydrogen Inorganic materials 0.000 claims description 2
- 239000001257 hydrogen Substances 0.000 claims description 2
- 125000004435 hydrogen atom Chemical class [H]* 0.000 claims description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims 1
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 12
- 238000006243 chemical reaction Methods 0.000 description 5
- YZZGJHDTYZOSIH-UHFFFAOYSA-N 2,3-dichloro-5-methylpyridine Chemical compound CC1=CN=C(Cl)C(Cl)=C1 YZZGJHDTYZOSIH-UHFFFAOYSA-N 0.000 description 4
- 239000000243 solution Substances 0.000 description 4
- JXQYOHGHAJITAK-UHFFFAOYSA-N 2,4-dichloro-4-methyl-5-oxopentanenitrile Chemical compound O=CC(Cl)(C)CC(Cl)C#N JXQYOHGHAJITAK-UHFFFAOYSA-N 0.000 description 3
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 3
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 3
- 229910000041 hydrogen chloride Inorganic materials 0.000 description 3
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- QUSNBJAOOMFDIB-UHFFFAOYSA-N Ethylamine Chemical compound CCN QUSNBJAOOMFDIB-UHFFFAOYSA-N 0.000 description 2
- BAVYZALUXZFZLV-UHFFFAOYSA-N Methylamine Chemical compound NC BAVYZALUXZFZLV-UHFFFAOYSA-N 0.000 description 2
- 150000001299 aldehydes Chemical class 0.000 description 2
- PAFZNILMFXTMIY-UHFFFAOYSA-N cyclohexylamine Chemical compound NC1CCCCC1 PAFZNILMFXTMIY-UHFFFAOYSA-N 0.000 description 2
- 238000002474 experimental method Methods 0.000 description 2
- 239000002798 polar solvent Substances 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- NLHHRLWOUZZQLW-UHFFFAOYSA-N Acrylonitrile Chemical compound C=CC#N NLHHRLWOUZZQLW-UHFFFAOYSA-N 0.000 description 1
- 229910021580 Cobalt(II) chloride Inorganic materials 0.000 description 1
- GYCMBHHDWRMZGG-UHFFFAOYSA-N Methylacrylonitrile Chemical compound CC(=C)C#N GYCMBHHDWRMZGG-UHFFFAOYSA-N 0.000 description 1
- 229910021586 Nickel(II) chloride Inorganic materials 0.000 description 1
- 101150066742 TRI1 gene Proteins 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- 230000004888 barrier function Effects 0.000 description 1
- 150000005753 chloropyridines Chemical group 0.000 description 1
- 238000004587 chromatography analysis Methods 0.000 description 1
- GPAYUJZHTULNBE-UHFFFAOYSA-N diphenylphosphine Chemical compound C=1C=CC=CC=1PC1=CC=CC=C1 GPAYUJZHTULNBE-UHFFFAOYSA-N 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- 238000004817 gas chromatography Methods 0.000 description 1
- 230000002363 herbicidal effect Effects 0.000 description 1
- 239000002917 insecticide Substances 0.000 description 1
- 239000000543 intermediate Substances 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- QSHDDOUJBYECFT-UHFFFAOYSA-N mercury Chemical compound [Hg] QSHDDOUJBYECFT-UHFFFAOYSA-N 0.000 description 1
- 229910052753 mercury Inorganic materials 0.000 description 1
- QMMRZOWCJAIUJA-UHFFFAOYSA-L nickel dichloride Chemical compound Cl[Ni]Cl QMMRZOWCJAIUJA-UHFFFAOYSA-L 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 238000007363 ring formation reaction Methods 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 239000011550 stock solution Substances 0.000 description 1
- 125000003866 trichloromethyl group Chemical group ClC(Cl)(Cl)* 0.000 description 1
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 1
- 150000004072 triols Chemical class 0.000 description 1
- 238000005292 vacuum distillation Methods 0.000 description 1
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
- C07D213/61—Halogen atoms or nitro radicals
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Pyridine Compounds (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Description
DK 157014 B
Opfindelsen angâr fremsti11ing af ha 1ogensubstituerede pyridi-ner ved en base- og/eller overgangsmetal-katalyseret ringslut-ning af subst i tuerede 5-oxo-pentan-l-ni tri 1er.
5 Europæisk patentansogning nr. 46.735 omhandler fremstilling af chlorpyridiner substitueret med methyl-, trichlormethy1 - eller trif 1uormethylgrupper ved addition af det tilsvarende aldehyd til acrylonitri1, methacrylonitri 1 eller α-trifluormethacrylo-nitril i nærværelse af en katalysator, samt cyklisering af det 10 fremkomne mellemprodukt i nærværelse af hydrogenchlorid eller et stof, som danner hydrogenchlorid under reaktionsbetingel-serne. Ved den omhandlede fremgangsmàde kan man sâledes frem-stille 2,3-dichlor-5-methylpyridin ved cyklisering af 2,4-di-chlor-4-methyl-5-oxopentannitri 1 i nærværelse af hydrogench1o-15 rid med Cu-pulver som katalysator ved 150°C og i et udbytte pâ 65 %.
Opfindelsen angâr en fremgangsmàde til fremstiΠing af halo-gensubstituerede pyridiner med formlen: 20 25 hvori R* er Cj-C^alkyl, phenyl eller hydrogen, R2 er Cl eller Br, og R3 er Cl, Br eller F, og fremgangsmàden er ejendommelig ved, at den omfatter cyklisering af en forbindelse med form-1 en : 30 R2 R3
I I
Rl-C-CH2-C-H
I I
35 CHO CN
hvori Rl, R2 og R3 er som ovenfor anfart, i nærværelse af en katalytisk mængde af mindst én basisk organisk amin og/eller 2
DK 157 014 B
en overgangsmetalkatalysator ved en temperatur i intervallet 25 til 250°C og i nærværelse af et indifferent polært oplos-ni ngsmiddel.
5 Ved fremgangsmâden ifalge opfindelsen opnâs den onskede for-bindelse i et udbytte pâ mere end 70%.
Forbindelserne fremstillet ved fremgangsmâden if0lge opfindelsen anvendes fordelagtigt som me!lemprodukter til fremstillin-10 gen af forbindelser med insekticid og/eller herbicid virkning, f.eks. som beskrevet i europæisk patentansogning nr. 46.735.
Reaktionen kan udfores ved en hvilken som helst temperatur fra 25°C til 250*C, men udfores fortrinsvis ved temperaturer pâ 70 15 - 250°C og helst ved temperaturer pâ 200 - 220°C.
Enhver basisk organisk amin, sâsom f.eks. ethylamin, methyl-amin og cyklohexylamin, kan anvendes, selv om isopropylamin foretrækkes.
20
Overgangsmetalkatalysatoren kan være enhver overgangsmetalkatalysator, sâsom f.eks. NiCl2- eller CoCl2((06Η5)3Ρ)2· Den fo-retrukne katalysator er nikkeldichlor-bis(triphenylphosphin). Reaktionen udfæres som nævnt i et egnet indifferent polært op-25 lesningsmiddel, fortrinsvis et ni triloplosningsmiddel og helst acetoni tri1.
Opfindelsen illustreres yderligere af de felgende eksempler.
30 Eksempel 1. Fremstilling af 2,3-dichlor-5-methylpyridin.
En oplosning af 32,343 g 2,4-dichlor-4-methyl-5-oxopentanni-tril i 150 ml acetonitril og indeholdende 300 mg nikkel-di= chlor-bis(triphenylphosphin) pumpedes gennem et nikkelspi-35 ralror med et volumen pâ ca. 30 ml ved en hastighed pâ 2,0 - 2,5 ml/min.. Oplosningen var blevet forvarmet til 200 - 210°C ved et tryk pâ 1.825 kPa.
3
DK 157014 B
Gaskromatografisk analyse (G.C.) viste 90% omdannelse af alde-hyd med et udbytte af 2,3-dichlor-5-methylpyridin pâ 77%.
Eksempel 2.
5 Det ovenfor anforte eksperiment blev gentaget, med undtagelse af, at der anvendtes 30,908 g af oxonitrilen, og at opl0snîngen indeholdt 3 ml isopropylamin ud over nikkelkatalysatoren.
Analyse ved hjælp af G.C. viste en omdannelse pâ 94,3% og et udbytte pâ 23,9 g (90,1%).
10
Eksempel 3.
Det ovenfor anforte eksperiment blev gentaget, med undtagelse af, at der anvendtes 31,7 g af oxonitrilen, og ca. 1 vægt% 15 (3,1 g) isopropylamin anvendtes som den eneste katalysator.
Udbyttet var 80% (G.C.).
Eksempel 4.
2o En oplosning af 32,1 g 2,4-dichlor-4-methyl-5-oxopentannitril i 250 ml acetonitril indeholdende 3 ml isopropylamin og ca.
300 mg m'kkeldichlor-bis(tn'phenylphosphin) opvarmedes med tilbagesvaling i 48 timer. Det overskydende acetonitril fjern-edes dernæst ved vakuumdestillation, og remanensen kolbedestil-25 leredes ved 85 - 90°C og 5 mm Hg i et kugleror. Udbyttet var 27,0 g 2,3-dichlor-5-methylpyridin (86%), der var isoleret som et hvidt fast stof.
Eksempel 5.
30
En stamoplosning indeholdende 30 g 2,4-dichlor-4-methyl-5-oxopentannitril i 150 ml acetonitril fremstilledes, og por-tioner pâ 15 - 20 ml blev udtaget og anbragt i 50 ml Fisher-Porter-flasker. De anforte katalysatorer (20 μΐ) blev der-35 nasst hver for sig sat til de forskellige f lasker. Reaktions- blandingerne anbragtes dernæst i et oliebad, der var forvarmet til 185°C, og fik lov at reagere i den anforte tid, hvorefter de analyseredes ved gaskromatografi. Resultaterne var som folger:
Claims (7)
1. Fremgangsmâde til fremstilling af halogensubstituerede py-20 ridiner med formlen °T R2 25 hvori Rl er C^-C4-alkyl, phenyl eller hydrogen, R2 er Cl eller Br, og R3 er Cl, Br eller F, kendetegnet ved, at den omfatter cyklisering af en forbindelse med formlen 30 R2 R3 I I Rl-C-CH2-C-H I I
35 CHO CN hvori Rl, R2 og R3 er som ovenfor anfort, i nærværelse af en katalytisk mængde af mindst én basisk organisk amin og/eller DK 157014 B en overgangsmeta1kata1ysator ved en temperatur i intervallet 25 til 250°C og i nærværelse af et indifferent polært oplos-n i ngsm i dde1.
2. Fremgangsmâde if0lge krav 1, kendetegnet ved, at Rl er methyl, og r2 og R3 er Cl.
3. Fremgangsmâde ifolge krav 1, kendetegnet ved, at Rl er ethyl, og r2 og R3 er Cl. 10
4. Fremgangsmâde ifelge krav 1, kendetegnet ved, at den organiske amin er isopropy1 amin.
5. Fremgangsmâde ifolge krav 2, kendetegnet ved, 15 at katalysatoren er nikkeldichlor-bis(triphenylphosphin).
6. Fremgangsmâde ifolge krav 5, kendetegnet ved, at temperaturen er 70 - 250°C.
7. Fremgangsmâde if.olge krav 1, kendetegnet ved, at katalysatoren omfatter en organisk amin og nikkeldichlor-bis(triphenylphosphin). 25 30 35
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US06/436,231 US4435573A (en) | 1982-10-25 | 1982-10-25 | Process for the preparation of substituted pyridines |
| US43623182 | 1982-10-25 |
Publications (4)
| Publication Number | Publication Date |
|---|---|
| DK17784D0 DK17784D0 (da) | 1984-01-16 |
| DK17784A DK17784A (da) | 1985-07-17 |
| DK157014B true DK157014B (da) | 1989-10-30 |
| DK157014C DK157014C (da) | 1990-03-26 |
Family
ID=23731634
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DK017784A DK157014C (da) | 1982-10-25 | 1984-01-16 | Fremgangsmaade til fremstilling af halogensubstituerede pyridiner |
Country Status (9)
| Country | Link |
|---|---|
| US (1) | US4435573A (da) |
| EP (1) | EP0149291B1 (da) |
| JP (1) | JPS60152466A (da) |
| KR (1) | KR900004040B1 (da) |
| BR (1) | BR8400598A (da) |
| DE (1) | DE3471302D1 (da) |
| DK (1) | DK157014C (da) |
| HU (1) | HU194173B (da) |
| IL (1) | IL70659A (da) |
Families Citing this family (10)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0113467B1 (de) * | 1980-08-27 | 1986-04-30 | Ciba-Geigy Ag | 2,2-Dichlor-3,3,3-trifluorpropionaldehyd und Verfahren zu seiner Herstellung |
| US4577028A (en) * | 1981-10-20 | 1986-03-18 | Ciba-Geigy Corporation | 5-Haloalkyl-pyridines |
| US4435573A (en) * | 1982-10-25 | 1984-03-06 | The Dow Chemical Company | Process for the preparation of substituted pyridines |
| US5053516A (en) * | 1984-05-23 | 1991-10-01 | Ici Americas Inc. | Synthesis of 2-substituted-5-methylpyridines from methylcyclobutanecarbonitrile, valeronitrile and pentenonitrile intermediates |
| US5084576A (en) * | 1985-12-20 | 1992-01-28 | The Dow Chemical Company | 2-hydrocarbyl-3,6-dichloropyridine compounds |
| US5106984A (en) * | 1985-12-20 | 1992-04-21 | The Dow Chemical Company | 2-hydrocarbyl-3,6-dichloropyridines and their preparation |
| IL86341A (en) * | 1988-05-11 | 1992-02-16 | Pamol Ltd | Preparation of polychloropyridine derivatives and intermediates therefor |
| US4996323A (en) * | 1989-05-12 | 1991-02-26 | The Dow Chemical Company | Process for the preparation of 3,5,6-trichloropyridin-2-ol |
| US5229519A (en) * | 1992-03-06 | 1993-07-20 | Reilly Industries, Inc. | Process for preparing 2-halo-5-halomethylpyridines |
| CN113402452B (zh) * | 2021-07-29 | 2022-08-02 | 上海垚翀化工科技有限公司 | 一种制备2-氯-5-取代吡啶的方法 |
Family Cites Families (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4245098A (en) * | 1978-12-05 | 1981-01-13 | Ciba-Geigy Corporation | Process for producing 2,3,5-trichloropyridine, 2,4,4-trichloro-4-formyl-butyronitrile as a novel compound and a process for producing it |
| EP0113467B1 (de) * | 1980-08-27 | 1986-04-30 | Ciba-Geigy Ag | 2,2-Dichlor-3,3,3-trifluorpropionaldehyd und Verfahren zu seiner Herstellung |
| ZA815906B (en) * | 1980-08-27 | 1982-08-25 | Ciba Geigy | Process for the production of chloropyridines substituted by methyl,trichloromethyl or trifluoromethyl groups |
| US4435573A (en) * | 1982-10-25 | 1984-03-06 | The Dow Chemical Company | Process for the preparation of substituted pyridines |
-
1982
- 1982-10-25 US US06/436,231 patent/US4435573A/en not_active Expired - Lifetime
-
1984
- 1984-01-11 IL IL70659A patent/IL70659A/xx not_active IP Right Cessation
- 1984-01-16 DE DE8484300241T patent/DE3471302D1/de not_active Expired
- 1984-01-16 EP EP84300241A patent/EP0149291B1/en not_active Expired
- 1984-01-16 DK DK017784A patent/DK157014C/da not_active IP Right Cessation
- 1984-01-19 HU HU84202A patent/HU194173B/hu not_active IP Right Cessation
- 1984-01-20 JP JP59008402A patent/JPS60152466A/ja active Granted
- 1984-01-24 KR KR1019840000294A patent/KR900004040B1/ko not_active Expired
- 1984-02-07 BR BR8400598A patent/BR8400598A/pt not_active IP Right Cessation
Also Published As
| Publication number | Publication date |
|---|---|
| IL70659A (en) | 1987-08-31 |
| DK17784D0 (da) | 1984-01-16 |
| US4435573A (en) | 1984-03-06 |
| HUT36803A (en) | 1985-10-28 |
| EP0149291B1 (en) | 1988-05-18 |
| KR850003397A (ko) | 1985-06-17 |
| KR900004040B1 (ko) | 1990-06-09 |
| DK157014C (da) | 1990-03-26 |
| DE3471302D1 (en) | 1988-06-23 |
| JPH0518827B2 (da) | 1993-03-15 |
| JPS60152466A (ja) | 1985-08-10 |
| HU194173B (en) | 1988-01-28 |
| EP0149291A1 (en) | 1985-07-24 |
| DK17784A (da) | 1985-07-17 |
| BR8400598A (pt) | 1985-09-17 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PBP | Patent lapsed |