RU2013139300A - Способ получения 4-амино-3-хлор-5-фтор-6-(замещенных)пиколинатов - Google Patents
Способ получения 4-амино-3-хлор-5-фтор-6-(замещенных)пиколинатов Download PDFInfo
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- RU2013139300A RU2013139300A RU2013139300/04A RU2013139300A RU2013139300A RU 2013139300 A RU2013139300 A RU 2013139300A RU 2013139300/04 A RU2013139300/04 A RU 2013139300/04A RU 2013139300 A RU2013139300 A RU 2013139300A RU 2013139300 A RU2013139300 A RU 2013139300A
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- ARMLHIZMMUSZAS-UHFFFAOYSA-N N#Cc(nc(c(F)c1F)F)c1Cl Chemical compound N#Cc(nc(c(F)c1F)F)c1Cl ARMLHIZMMUSZAS-UHFFFAOYSA-N 0.000 description 1
Classifications
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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
- C07D213/84—Nitriles
-
- 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
- C07D213/72—Nitrogen atoms
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- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
- A01N43/34—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one nitrogen atom as the only ring hetero atom
- A01N43/40—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one nitrogen atom as the only ring hetero atom six-membered rings
-
- 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
- C07D213/79—Acids; Esters
-
- 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
- C07D213/79—Acids; Esters
- C07D213/803—Processes of preparation
-
- 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
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- Agronomy & Crop Science (AREA)
- Pest Control & Pesticides (AREA)
- Plant Pathology (AREA)
- Health & Medical Sciences (AREA)
- Engineering & Computer Science (AREA)
- Dentistry (AREA)
- General Health & Medical Sciences (AREA)
- Wood Science & Technology (AREA)
- Zoology (AREA)
- Environmental Sciences (AREA)
- Pyridine Compounds (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Abstract
1. Способ получения 4-амино-3-хлор-5-фтор-6-(замещенного)пиколината формулы Iв которойR представляет собой (C-C)алкил, циклопропил, (C-C)алкенил или фенил, содержащий от 1 до 4 заместителей, в качестве которых независимо выбирают галоген, (C-C)алкил, (C-C)галогеналкил, (C-C)алкокси или (C-C)галогеналкокси;Rпредставляет собой (C-C)алкил или незамещенный или замещенный (C-C)арилалкил;который включает следующие стадии:a) фторирование 3,4,5,6-тетрахлорпиколинонитрила (формула A)источником фторид-ионов для получения 3-хлор-4,5,6-трифторпиколинонитрила (формула B)b) аминирование 3-хлор-4,5,6-трифтор-2-пиколинонитрила (формула B) аммиаком для получения 4-амино-3-хлор-5,6-дифторпиколинонитрила (формула C)c) замещение фторзаместителя в положении 6 4-амино-3-хлор-5,6-дифторпиколинонитрила (формула C) с помощью бромоводорода (HBr), хлороводорода (HCl) или йодоводорода (HI) и гидролиз нитрила для получения 4-амино-3-хлор-5-фтор-6-галогенпиколинамида формулы Dв которой L представляет собой Br, Cl или I;d) этерификацию 4-амино-3-хлор-5-фтор-6-галогенпиколинамида формулы D сильной кислотой и спиртом (ROH) для получения 4-амино-3-хлор-5-фтор-6-галогенпиколината формулы Eв которой L и Rявляются такими, как определено выше; иe) сочетание 4-амино-3-хлор-5-фтор-6-галогенпиколината формулы E с арил-, алкил- или алкенилметаллоорганическим соединением формулы Fв которой R является таким, как определено выше, и Met представляет собой Zn-галогенид, Zn-R, три-((C-C)алкил)олово, медь, или B(OR)(OR), где Rи Rнезависимо друг от друга представляют собой водород или (C-C)алкил, или совместно образуют этиленовую или пропиленовую группу в присутствии содержащего переходный металл катализатора, для получения 4-амино-3-хлор-5-фтор-6-(
Claims (2)
1. Способ получения 4-амино-3-хлор-5-фтор-6-(замещенного)пиколината формулы I
в которой
R представляет собой (C1-C4)алкил, циклопропил, (C2-C4)алкенил или фенил, содержащий от 1 до 4 заместителей, в качестве которых независимо выбирают галоген, (C1-C4)алкил, (C1-C4)галогеналкил, (C1-C4)алкокси или (C1-C4)галогеналкокси;
R1 представляет собой (C1-C12)алкил или незамещенный или замещенный (C7-C11)арилалкил;
который включает следующие стадии:
a) фторирование 3,4,5,6-тетрахлорпиколинонитрила (формула A)
источником фторид-ионов для получения 3-хлор-4,5,6-трифторпиколинонитрила (формула B)
b) аминирование 3-хлор-4,5,6-трифтор-2-пиколинонитрила (формула B) аммиаком для получения 4-амино-3-хлор-5,6-дифторпиколинонитрила (формула C)
c) замещение фторзаместителя в положении 6 4-амино-3-хлор-5,6-дифторпиколинонитрила (формула C) с помощью бромоводорода (HBr), хлороводорода (HCl) или йодоводорода (HI) и гидролиз нитрила для получения 4-амино-3-хлор-5-фтор-6-галогенпиколинамида формулы D
в которой L представляет собой Br, Cl или I;
d) этерификацию 4-амино-3-хлор-5-фтор-6-галогенпиколинамида формулы D сильной кислотой и спиртом (R1OH) для получения 4-амино-3-хлор-5-фтор-6-галогенпиколината формулы E
в которой L и R1 являются такими, как определено выше; и
e) сочетание 4-амино-3-хлор-5-фтор-6-галогенпиколината формулы E с арил-, алкил- или алкенилметаллоорганическим соединением формулы F
в которой R является таким, как определено выше, и Met представляет собой Zn-галогенид, Zn-R, три-((C1-C4)алкил)олово, медь, или B(OR2)(OR3), где R2 и R3 независимо друг от друга представляют собой водород или (C1-C4)алкил, или совместно образуют этиленовую или пропиленовую группу в присутствии содержащего переходный металл катализатора, для получения 4-амино-3-хлор-5-фтор-6-(замещенного)пиколината формулы I.
2. Соединение формулы:
a)
в которой X и Y независимо представляют собой F или Cl;
b)
в которой X и Y независимо представляют собой F или Cl при том условии, что, по меньшей мере, один из X и Y представляет собой F;
c)
в которой W1 представляет собой F, Cl, Br или I;
d)
в которой W2 представляет собой Cl, Br или I; или
e)
в которой R1 представляет собой (C1-C12)алкил или незамещенный или замещенный (C7-C11)арилалкил, и W3 представляет собой Br или I.
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US201161435966P | 2011-01-25 | 2011-01-25 | |
| US61/435,966 | 2011-01-25 | ||
| PCT/US2012/022285 WO2012103041A2 (en) | 2011-01-25 | 2012-01-24 | Process for the preparation of 4-amino-3-chloro-5-fluoro-6-(substituted) picolinates |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| RU2545021C1 RU2545021C1 (ru) | 2015-03-27 |
| RU2013139300A true RU2013139300A (ru) | 2015-04-10 |
Family
ID=46544648
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| RU2013139300/04A RU2545021C1 (ru) | 2011-01-25 | 2012-01-24 | Способ получения 4-амино-3-хлор-5-фтор-6-(замещенных)пиколинатов |
Country Status (20)
| Country | Link |
|---|---|
| US (3) | US20120190857A1 (ru) |
| EP (1) | EP2668163B1 (ru) |
| JP (1) | JP5739018B2 (ru) |
| KR (1) | KR101537879B1 (ru) |
| CN (2) | CN103874685B (ru) |
| AR (1) | AR085022A1 (ru) |
| AU (1) | AU2012209277B2 (ru) |
| BR (2) | BR112013019025A2 (ru) |
| CA (1) | CA2825475C (ru) |
| CO (1) | CO6731125A2 (ru) |
| HK (2) | HK1213875A1 (ru) |
| IL (1) | IL227646A (ru) |
| MX (1) | MX342328B (ru) |
| PL (1) | PL2668163T3 (ru) |
| RU (1) | RU2545021C1 (ru) |
| SG (1) | SG192093A1 (ru) |
| TW (1) | TWI592401B (ru) |
| UA (1) | UA106945C2 (ru) |
| WO (1) | WO2012103041A2 (ru) |
| ZA (1) | ZA201305577B (ru) |
Families Citing this family (14)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| TWI592401B (zh) | 2011-01-25 | 2017-07-21 | 陶氏農業科學公司 | 用於製備４－胺基－３－氯－５－氟－６－（經取代的）吡啶甲酸酯的方法（一） |
| US9637505B2 (en) | 2013-03-15 | 2017-05-02 | Dow Agrosciences Llc | 4-amino-6-(heterocyclic)picolinates and 6-amino-2-(heterocyclic)pyrimidine-4-carboxylates and their use as herbicides |
| US9113629B2 (en) | 2013-03-15 | 2015-08-25 | Dow Agrosciences Llc | 4-amino-6-(4-substituted-phenyl)-picolinates and 6-amino-2-(4-substituted-phenyl)-pyrimidine-4-carboxylates and their use as herbicides |
| CN105209452A (zh) | 2013-03-15 | 2015-12-30 | 美国陶氏益农公司 | 4-氨基-6-(杂环基)吡啶-2-甲酸酯和6-氨基-2-(杂环基)嘧啶-4-羧酸酯以及它们作为除草剂的用途 |
| WO2014150809A1 (en) | 2013-03-15 | 2014-09-25 | Dow Agrosciences Llc | Novel 4-aminopyridine and 6-aminopyrimidine carboxylates as herbicides |
| TW201609652A (zh) | 2013-11-12 | 2016-03-16 | 陶氏農業科學公司 | 用於氟化化合物之過程（三） |
| TW201609651A (zh) | 2013-11-12 | 2016-03-16 | 陶氏農業科學公司 | 用於氟化化合物之過程（一） |
| TW201524956A (zh) * | 2013-11-12 | 2015-07-01 | Dow Agrosciences Llc | 用於氟化化合物之過程（二） |
| TWI726900B (zh) | 2015-08-04 | 2021-05-11 | 美商陶氏農業科學公司 | 用於氟化化合物之過程 |
| CA3023935A1 (en) | 2016-05-19 | 2017-11-23 | Dow Agrosciences Llc | Synthesis of 6-aryl-4-aminopicolinates and 2-aryl-6-aminopyrimidine-4-carboxylates by direct suzuki coupling |
| CN107954925A (zh) * | 2016-10-18 | 2018-04-24 | 内蒙古佳瑞米精细化工有限公司 | 一种2,3-二氯-5-三氟甲基吡啶前杂的去除方法 |
| US11401242B2 (en) | 2018-09-19 | 2022-08-02 | Corteva Agriscience Llc | Preparation of halogen analogs of picloram |
| US20230174490A1 (en) | 2020-03-18 | 2023-06-08 | Corteva Agriscience Llc | Improved synthesis of 6-aryl-4-aminopicolinates |
| WO2021188639A1 (en) | 2020-03-18 | 2021-09-23 | Corteva Agriscience Llc | Improved synthesis of 4-amino-6-(heterocyclic)picolinates |
Family Cites Families (16)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3285925A (en) * | 1962-03-06 | 1966-11-15 | Dow Chemical Co | Amino-trichloropicolinic acid compounds |
| US3803159A (en) * | 1967-12-26 | 1974-04-09 | Dow Chemical Co | Fluorine containing cyanopyridines |
| US3629424A (en) * | 1967-12-26 | 1971-12-21 | Dow Chemical Co | Cyanofluoropyridines and fungicidal compositions and methods for using the same |
| US4336384A (en) * | 1981-04-23 | 1982-06-22 | The Dow Chemical Company | Preparation of 4-amino-3,5,6-trichloropicolinic acid |
| US5710106A (en) * | 1996-02-22 | 1998-01-20 | American Cyanamid Company | Substituted pyridine herbicidal agents |
| FR2803592A1 (fr) * | 2000-01-06 | 2001-07-13 | Aventis Cropscience Sa | Nouveaux derives de l'acide 3-hydroxypicolinique, leur procede de preparation et compositions fongicides les contenant. |
| US6297197B1 (en) | 2000-01-14 | 2001-10-02 | Dow Agrosciences Llc | 4-aminopicolinates and their use as herbicides |
| PL212932B1 (pl) * | 2000-01-14 | 2012-12-31 | Dow Agrosciences Llc | Pochodne 4-aminopikolinianowe, kompozycja herbicydowa zawierajaca te zwiazki oraz sposób kontrolowania niepozadanej wegetacji |
| AR037228A1 (es) * | 2001-07-30 | 2004-11-03 | Dow Agrosciences Llc | Compuestos del acido 6-(aril o heteroaril)-4-aminopicolinico, composicion herbicida que los comprende y metodo para controlar vegetacion no deseada |
| UA82358C2 (ru) * | 2003-04-02 | 2008-04-10 | Дау Агросайенсиз Ллс | 6-алкил или фенил-4-аминопиколинаты, гербицидная композиция, способ борьбы с нежелательной растительностью |
| JP5059779B2 (ja) * | 2006-01-13 | 2012-10-31 | ダウ アグロサイエンシィズ エルエルシー | ６−（多置換アリール）−４−アミノピコリネートおよび除草剤としてのそれらの使用 |
| DK2332914T3 (da) * | 2007-10-02 | 2013-06-17 | Dow Agrosciences Llc | Substituerede 4-aminopicolinsyrer og deres anvendelse som herbicider |
| US8252938B2 (en) * | 2009-06-08 | 2012-08-28 | Dow Agrosciences, Llc. | Process for the preparation of 6-(aryl)-4-aminopicolinates |
| GB0910766D0 (en) * | 2009-06-22 | 2009-08-05 | Syngenta Ltd | Chemical compounds |
| GB201008290D0 (en) * | 2010-05-18 | 2010-06-30 | Syngenta Ltd | Chemical compounds |
| TWI592401B (zh) | 2011-01-25 | 2017-07-21 | 陶氏農業科學公司 | 用於製備４－胺基－３－氯－５－氟－６－（經取代的）吡啶甲酸酯的方法（一） |
-
2012
- 2012-01-20 TW TW101102582A patent/TWI592401B/zh not_active IP Right Cessation
- 2012-01-24 CN CN201280014336.2A patent/CN103874685B/zh not_active Expired - Fee Related
- 2012-01-24 BR BR112013019025A patent/BR112013019025A2/pt not_active Application Discontinuation
- 2012-01-24 PL PL12739865T patent/PL2668163T3/pl unknown
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