KR100567197B1 - 2-하이드록시-6-트리플루오로메틸피리딘의 화학적 제조 방법 - Google Patents
2-하이드록시-6-트리플루오로메틸피리딘의 화학적 제조 방법 Download PDFInfo
- Publication number
- KR100567197B1 KR100567197B1 KR1020017002721A KR20017002721A KR100567197B1 KR 100567197 B1 KR100567197 B1 KR 100567197B1 KR 1020017002721 A KR1020017002721 A KR 1020017002721A KR 20017002721 A KR20017002721 A KR 20017002721A KR 100567197 B1 KR100567197 B1 KR 100567197B1
- Authority
- KR
- South Korea
- Prior art keywords
- trifluoromethylpyridine
- hydroxy
- fluoro
- chloro
- alkali metal
- 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 - Lifetime
Links
- XXRUAAOADAPPII-UHFFFAOYSA-N 6-(trifluoromethyl)-1h-pyridin-2-one Chemical compound OC1=CC=CC(C(F)(F)F)=N1 XXRUAAOADAPPII-UHFFFAOYSA-N 0.000 title claims abstract description 45
- 238000005285 chemical preparation method Methods 0.000 title 1
- IZOIOCQPMHHDHN-UHFFFAOYSA-N 2-fluoro-6-(trifluoromethyl)pyridine Chemical compound FC1=CC=CC(C(F)(F)F)=N1 IZOIOCQPMHHDHN-UHFFFAOYSA-N 0.000 claims abstract description 41
- 238000000034 method Methods 0.000 claims abstract description 26
- ADVQMCQMDHBTHJ-UHFFFAOYSA-N 2-chloro-6-(trifluoromethyl)pyridine Chemical compound FC(F)(F)C1=CC=CC(Cl)=N1 ADVQMCQMDHBTHJ-UHFFFAOYSA-N 0.000 claims abstract description 21
- 150000008044 alkali metal hydroxides Chemical class 0.000 claims abstract description 14
- 238000002360 preparation method Methods 0.000 claims abstract description 14
- 239000000203 mixture Substances 0.000 claims abstract description 9
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical group [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 claims description 62
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 16
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims description 8
- 238000004519 manufacturing process Methods 0.000 claims description 4
- 239000000126 substance Substances 0.000 claims description 4
- 150000001875 compounds Chemical class 0.000 claims description 3
- 239000007864 aqueous solution Substances 0.000 claims description 2
- BSKHPKMHTQYZBB-UHFFFAOYSA-N 2-methylpyridine Chemical compound CC1=CC=CC=N1 BSKHPKMHTQYZBB-UHFFFAOYSA-N 0.000 claims 1
- 239000011541 reaction mixture Substances 0.000 description 29
- 239000000047 product Substances 0.000 description 21
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 20
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 20
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 18
- 239000007858 starting material Substances 0.000 description 16
- 238000006243 chemical reaction Methods 0.000 description 15
- MSXVEPNJUHWQHW-UHFFFAOYSA-N 2-methylbutan-2-ol Chemical compound CCC(C)(C)O MSXVEPNJUHWQHW-UHFFFAOYSA-N 0.000 description 14
- 238000010992 reflux Methods 0.000 description 14
- 239000002585 base Substances 0.000 description 12
- 239000000243 solution Substances 0.000 description 11
- 239000000706 filtrate Substances 0.000 description 8
- 230000007062 hydrolysis Effects 0.000 description 8
- 238000006460 hydrolysis reaction Methods 0.000 description 8
- 239000002002 slurry Substances 0.000 description 7
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 6
- UBQKCCHYAOITMY-UHFFFAOYSA-N pyridin-2-ol Chemical compound OC1=CC=CC=N1 UBQKCCHYAOITMY-UHFFFAOYSA-N 0.000 description 6
- 235000011121 sodium hydroxide Nutrition 0.000 description 6
- 239000002904 solvent Substances 0.000 description 6
- 238000001035 drying Methods 0.000 description 4
- 238000004817 gas chromatography Methods 0.000 description 4
- DKGAVHZHDRPRBM-UHFFFAOYSA-N tert-butyl alcohol Substances CC(C)(C)O DKGAVHZHDRPRBM-UHFFFAOYSA-N 0.000 description 4
- OKDGRDCXVWSXDC-UHFFFAOYSA-N 2-chloropyridine Chemical compound ClC1=CC=CC=N1 OKDGRDCXVWSXDC-UHFFFAOYSA-N 0.000 description 3
- 238000005481 NMR spectroscopy Methods 0.000 description 3
- 238000002844 melting Methods 0.000 description 3
- 230000008018 melting Effects 0.000 description 3
- NLKNQRATVPKPDG-UHFFFAOYSA-M potassium iodide Chemical compound [K+].[I-] NLKNQRATVPKPDG-UHFFFAOYSA-M 0.000 description 3
- 239000007787 solid Substances 0.000 description 3
- 239000003513 alkali Substances 0.000 description 2
- 238000001914 filtration Methods 0.000 description 2
- LVWZTYCIRDMTEY-UHFFFAOYSA-N metamizole Chemical compound O=C1C(N(CS(O)(=O)=O)C)=C(C)N(C)N1C1=CC=CC=C1 LVWZTYCIRDMTEY-UHFFFAOYSA-N 0.000 description 2
- 150000003222 pyridines Chemical class 0.000 description 2
- 238000011084 recovery Methods 0.000 description 2
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 2
- 150000003509 tertiary alcohols Chemical class 0.000 description 2
- ATRQECRSCHYSNP-UHFFFAOYSA-N 2-(trifluoromethyl)pyridine Chemical compound FC(F)(F)C1=CC=CC=N1 ATRQECRSCHYSNP-UHFFFAOYSA-N 0.000 description 1
- XKWSQIMYNVLGBO-UHFFFAOYSA-N 5-nitro-1h-pyridin-2-one Chemical compound OC1=CC=C([N+]([O-])=O)C=N1 XKWSQIMYNVLGBO-UHFFFAOYSA-N 0.000 description 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 1
- 229910000792 Monel Inorganic materials 0.000 description 1
- 229910000990 Ni alloy Inorganic materials 0.000 description 1
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
- 239000002202 Polyethylene glycol Substances 0.000 description 1
- 229910000102 alkali metal hydride Inorganic materials 0.000 description 1
- 150000008046 alkali metal hydrides Chemical class 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- 239000003849 aromatic solvent Substances 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- 238000010924 continuous production Methods 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 150000003983 crown ethers Chemical class 0.000 description 1
- 125000000118 dimethyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 230000007613 environmental effect Effects 0.000 description 1
- 210000003608 fece Anatomy 0.000 description 1
- 229910000856 hastalloy Inorganic materials 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 230000003301 hydrolyzing effect Effects 0.000 description 1
- 239000012535 impurity Substances 0.000 description 1
- 229910001026 inconel Inorganic materials 0.000 description 1
- 150000002576 ketones Chemical class 0.000 description 1
- 238000011031 large-scale manufacturing process Methods 0.000 description 1
- 239000010871 livestock manure Substances 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 150000007522 mineralic acids Chemical class 0.000 description 1
- 239000003607 modifier Substances 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 230000000737 periodic effect Effects 0.000 description 1
- 239000000575 pesticide Substances 0.000 description 1
- 239000003444 phase transfer catalyst Substances 0.000 description 1
- 150000004714 phosphonium salts Chemical class 0.000 description 1
- 239000003880 polar aprotic solvent Substances 0.000 description 1
- 229920001223 polyethylene glycol Polymers 0.000 description 1
- 238000004445 quantitative analysis Methods 0.000 description 1
- 150000003242 quaternary ammonium salts Chemical class 0.000 description 1
- 230000002441 reversible effect Effects 0.000 description 1
- 150000003462 sulfoxides Chemical class 0.000 description 1
- JRMUNVKIHCOMHV-UHFFFAOYSA-M tetrabutylammonium bromide Chemical compound [Br-].CCCC[N+](CCCC)(CCCC)CCCC JRMUNVKIHCOMHV-UHFFFAOYSA-M 0.000 description 1
- -1 xylene Chemical compound 0.000 description 1
- 239000008096 xylene Substances 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
- C07D213/62—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
- C07B—GENERAL METHODS OF ORGANIC CHEMISTRY; APPARATUS THEREFOR
- C07B41/00—Formation or introduction of functional groups containing oxygen
- C07B41/02—Formation or introduction of functional groups containing oxygen of hydroxy or O-metal groups
-
- 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
- C07D213/24—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 substituted hydrocarbon radicals attached to ring carbon atoms
- C07D213/26—Radicals substituted by halogen atoms or nitro radicals
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Pyridine Compounds (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Physical Or Chemical Processes And Apparatus (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GBGB9819235.4A GB9819235D0 (en) | 1998-09-03 | 1998-09-03 | Chemical process |
| GB9819235.4 | 1998-09-03 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| KR20010074916A KR20010074916A (ko) | 2001-08-09 |
| KR100567197B1 true KR100567197B1 (ko) | 2006-04-03 |
Family
ID=10838299
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| KR1020017002721A Expired - Lifetime KR100567197B1 (ko) | 1998-09-03 | 1999-09-02 | 2-하이드록시-6-트리플루오로메틸피리딘의 화학적 제조 방법 |
Country Status (14)
| Country | Link |
|---|---|
| US (1) | US6143899A (enExample) |
| EP (1) | EP1109788B1 (enExample) |
| JP (1) | JP4302322B2 (enExample) |
| KR (1) | KR100567197B1 (enExample) |
| CN (1) | CN1134416C (enExample) |
| AT (1) | ATE258547T1 (enExample) |
| AU (1) | AU5638399A (enExample) |
| BR (1) | BR9913401B1 (enExample) |
| DE (1) | DE69914493T2 (enExample) |
| DK (1) | DK1109788T3 (enExample) |
| ES (1) | ES2215397T3 (enExample) |
| GB (1) | GB9819235D0 (enExample) |
| IL (2) | IL141597A0 (enExample) |
| WO (1) | WO2000014068A1 (enExample) |
Families Citing this family (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB0016336D0 (en) | 2000-07-03 | 2000-08-23 | Zeneca Ltd | Chemical process |
| GB0016338D0 (en) | 2000-07-03 | 2000-08-23 | Zeneca Ltd | Chemical process |
| WO2015151116A2 (en) * | 2014-03-31 | 2015-10-08 | Jubilant Life Sciences Limited | Process for producing 2-fluoro-6-(trifluoromethyl)pyridine compounds |
| CN107759513A (zh) * | 2017-11-17 | 2018-03-06 | 山东汇盟生物科技有限公司 | 一种2‑羟基‑6‑三氟甲基吡啶的制备方法 |
| CN108997203B (zh) * | 2018-06-26 | 2020-08-14 | 江苏扬农化工集团有限公司 | 一种2,3-二氯-5-三氟甲基吡啶的高效提纯方法 |
Family Cites Families (15)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB288628A (en) * | 1927-04-14 | 1929-07-03 | Schering Kahlbaum Ag | Process for the manufacture of hydroxypyridine compounds |
| US3355456A (en) * | 1965-05-06 | 1967-11-28 | Dow Chemical Co | Production of monohalopyridinols |
| US3609158A (en) * | 1969-03-17 | 1971-09-28 | Dow Chemical Co | Certain substituted (pyridyl)-oxy acetic acid derivatives |
| US3711486A (en) * | 1969-03-17 | 1973-01-16 | Dow Chemical Co | Substituted(trifluoromethyl)pyridines |
| GB1303679A (enExample) * | 1970-06-30 | 1973-01-17 | ||
| US4108629A (en) * | 1973-03-19 | 1978-08-22 | The Dow Chemical Company | Herbicidal use of esters of aminohalopyridyloxy acids |
| US4038396A (en) * | 1975-02-24 | 1977-07-26 | Merck & Co., Inc. | Anti-inflammatory oxazole[4,5-b]pyridines |
| US4249009A (en) * | 1979-01-29 | 1981-02-03 | Reilly Tar & Chemical Corp. | Processes for preparing 2-chloro-5-trifluoromethylpyridine |
| US4474599A (en) * | 1982-07-14 | 1984-10-02 | The Dow Chemical Company | 1-(Pyridyl)-1H-1,2,3-triazole derivatives, and use as herbicidal agents |
| US4455313A (en) * | 1982-08-20 | 1984-06-19 | The Dow Chemical Company | Fungicidal control employing substituted pyridinols |
| JPS6348268A (ja) * | 1986-08-14 | 1988-02-29 | Ishihara Sangyo Kaisha Ltd | Ｎ−ピリジル−ｎ’−ベンゾイルウレア系化合物及びそれらを含有する殺虫剤 |
| JPH0822851B2 (ja) * | 1987-09-16 | 1996-03-06 | 北興化学工業株式会社 | ２，３，５−トリクロロピリジンの製造方法 |
| DE3814358A1 (de) * | 1988-04-28 | 1989-11-09 | Ruetgerswerke Ag | Verfahren zur herstellung von 2-hydroxypyridin |
| US4976946A (en) * | 1990-02-09 | 1990-12-11 | The Dow Chemical Company | Separation of potassium salts |
| GB9704795D0 (en) * | 1997-03-07 | 1997-04-23 | Zeneca Ltd | Chemical process |
-
1998
- 1998-09-03 GB GBGB9819235.4A patent/GB9819235D0/en not_active Ceased
-
1999
- 1999-09-02 JP JP2000568827A patent/JP4302322B2/ja not_active Expired - Lifetime
- 1999-09-02 AT AT99943100T patent/ATE258547T1/de active
- 1999-09-02 WO PCT/GB1999/002894 patent/WO2000014068A1/en not_active Ceased
- 1999-09-02 BR BRPI9913401-2A patent/BR9913401B1/pt not_active IP Right Cessation
- 1999-09-02 DE DE69914493T patent/DE69914493T2/de not_active Expired - Lifetime
- 1999-09-02 IL IL14159799A patent/IL141597A0/xx active IP Right Grant
- 1999-09-02 EP EP99943100A patent/EP1109788B1/en not_active Expired - Lifetime
- 1999-09-02 ES ES99943100T patent/ES2215397T3/es not_active Expired - Lifetime
- 1999-09-02 CN CNB998101761A patent/CN1134416C/zh not_active Expired - Lifetime
- 1999-09-02 AU AU56383/99A patent/AU5638399A/en not_active Abandoned
- 1999-09-02 DK DK99943100T patent/DK1109788T3/da active
- 1999-09-02 KR KR1020017002721A patent/KR100567197B1/ko not_active Expired - Lifetime
- 1999-09-03 US US09/390,049 patent/US6143899A/en not_active Expired - Lifetime
-
2001
- 2001-02-22 IL IL141597A patent/IL141597A/en not_active IP Right Cessation
Also Published As
| Publication number | Publication date |
|---|---|
| AU5638399A (en) | 2000-03-27 |
| CN1314889A (zh) | 2001-09-26 |
| CN1134416C (zh) | 2004-01-14 |
| JP4302322B2 (ja) | 2009-07-22 |
| EP1109788A1 (en) | 2001-06-27 |
| BR9913401B1 (pt) | 2010-07-13 |
| BR9913401A (pt) | 2001-05-22 |
| JP2002524447A (ja) | 2002-08-06 |
| US6143899A (en) | 2000-11-07 |
| IL141597A (en) | 2006-08-20 |
| EP1109788B1 (en) | 2004-01-28 |
| KR20010074916A (ko) | 2001-08-09 |
| DE69914493T2 (de) | 2004-07-22 |
| DE69914493D1 (de) | 2004-03-04 |
| IL141597A0 (en) | 2002-03-10 |
| DK1109788T3 (da) | 2004-06-01 |
| WO2000014068A1 (en) | 2000-03-16 |
| ES2215397T3 (es) | 2004-10-01 |
| GB9819235D0 (en) | 1998-10-28 |
| ATE258547T1 (de) | 2004-02-15 |
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