AR085020A1 - Proceso para preparar 4-amino-5-fluor-3-halo-6-(sustituidos)picolinatos e intermediarios de dicha sintesis - Google Patents
Proceso para preparar 4-amino-5-fluor-3-halo-6-(sustituidos)picolinatos e intermediarios de dicha sintesisInfo
- Publication number
- AR085020A1 AR085020A1 ARP120100232A ARP120100232A AR085020A1 AR 085020 A1 AR085020 A1 AR 085020A1 AR P120100232 A ARP120100232 A AR P120100232A AR P120100232 A ARP120100232 A AR P120100232A AR 085020 A1 AR085020 A1 AR 085020A1
- Authority
- AR
- Argentina
- Prior art keywords
- formula
- amino
- fluorine
- alkyl
- produce
- Prior art date
Links
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
- C07D213/78—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
-
- 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
-
- 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
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Pyridine Compounds (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Abstract
Reivindicación 1: Un proceso para la preparación de un 4-amino-5-flúor-3-halo-6-(substituido)picolinato de la fórmula (1) en donde W representa Cl, Br o I; R representa alquilo C1-4, ciclopropilo, alquenilo C2-4 o fenilo substituido con desde 1 hasta 4 substituyentes independientemente seleccionados desde el halógeno, alquilo C1-4, haloalquilo C1-4, alcoxi C1-4 o haloalcoxi C1-4; y R1 representa alquilo C1-12 o un arilalquilo C7-11 insubstituido o substituido; que comprende los siguientes pasos: a) la fluorización de 4,5,6-tricloropicolinonitrilo de fórmula (A) con una fuente de ión de fluoruro para producir el 4,5,6-triflúorpicolinonitrilo de fórmula (B); b) la aminación de 4,5,6-triflúorpicolinonitrilo de fórmula (B) con amoníaco para producir el 4-amino-5,6-diflúorpicolinonitrilo de fórmula (C); c) la hidrolización del nitrilo substituyente e intercambio del flúor substituyente en la posición-6 de 4-amino-5,6-diflúorpicolinonitrilo de fórmula (C) con un substituyente de iodo, bromo o cloro mediante el tratamiento con una fuente de ioduro, bromuro o cloruro para producir una 4-amino-5-flúor-6-halopicolinamida de la fórmula (D), en donde X representa Cl, Br o I; d) la esterificación de la 4-amino-5-flúor-6-halopicolinamida de la fórmula (D) con un alcohol (R1OH) y un ácido de Bronsted o Lewis para producir un 4-amino-5-flúor-6-halopicolinato de la fórmula (E) en donde R1 representa alquilo C1-12 o un arilalquilo C7-11 insubstituido o substituido; e) la halogenación del 4-amino-5-flúor-6-halopicolinato de la fórmula (E) con una fuente de halógeno para producir un 4-amino-5-flúor-3,6-dihalopicolinato de la fórmula (F), en donde W y X independientemente representan Cl, Br o I, y R1 es como fue definido previamente; y f) acoplar el 4-amino-5-flúor-3,6-dihalopicolinato de la fórmula (F) con un compuesto de metal de arilo, alquilo o alquenilo de la fórmula: R-Met, en donde R es como fue definido previamente y Met representa un Zn-haluro, Zn-R, tri-(alquil C1-4)estaño, cobre, o B(OR2)(OR3), donde R2 y R3 son independientes la una de la otra, hidrógeno, alquilo C1-4, o cuando son tomadas juntas forman un grupo etileno o propileno en la presencia de un catalizador de metal de transición, para producir el 4-amino-3-halo-5-flúor-6-(substituido)picolinato de la fórmula (1).
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US201161435936P | 2011-01-25 | 2011-01-25 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| AR085020A1 true AR085020A1 (es) | 2013-08-07 |
Family
ID=46544650
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| ARP120100232A AR085020A1 (es) | 2011-01-25 | 2012-01-24 | Proceso para preparar 4-amino-5-fluor-3-halo-6-(sustituidos)picolinatos e intermediarios de dicha sintesis |
Country Status (20)
| Country | Link |
|---|---|
| US (2) | US8754231B2 (es) |
| EP (1) | EP2667712B1 (es) |
| JP (1) | JP5781171B2 (es) |
| KR (2) | KR20150013334A (es) |
| CN (1) | CN103458689B (es) |
| AR (1) | AR085020A1 (es) |
| AU (1) | AU2012209281B2 (es) |
| BR (2) | BR102012001643A2 (es) |
| CA (1) | CA2825468C (es) |
| CO (1) | CO6731129A2 (es) |
| HK (1) | HK1188684A1 (es) |
| IL (1) | IL227647B (es) |
| MX (1) | MX338962B (es) |
| PL (1) | PL2667712T3 (es) |
| RU (1) | RU2542985C1 (es) |
| SG (1) | SG192101A1 (es) |
| TW (1) | TWI537252B (es) |
| UA (1) | UA109806C2 (es) |
| WO (1) | WO2012103045A1 (es) |
| ZA (1) | ZA201305582B (es) |
Families Citing this family (13)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN103763923B (zh) * | 2011-06-30 | 2016-08-17 | 陶氏益农公司 | 3-烷氧基-4-氨基-6-(取代的)吡啶甲酸酯、3-硫代烷基-4-氨基-6-(取代的)吡啶甲酸酯和3-氨基-4-氨基-6-(取代的)吡啶甲酸酯以及它们作为除草剂的用途 |
| AR091856A1 (es) | 2012-07-24 | 2015-03-04 | Dow Agrosciences Llc | Proceso para la preparacion de 4-amino-5-fluor-3-halo-6-(substituido) picolinatos |
| AR092355A1 (es) | 2012-07-24 | 2015-04-15 | Dow Agrosciences Llc | Fluoruros de fluoropicolinoilo y procesos para su preparacion |
| BR102013032022A2 (pt) * | 2012-12-13 | 2014-10-21 | Dow Agrosciences Llc | Processo para a preparação de 4-amino-5-fluoro-3-cloro-6-(substituído)picolinatos |
| BR102014028164A2 (pt) * | 2013-11-12 | 2015-09-08 | Dow Agrosciences Llc | processo para fluoração de compostos |
| BR102014028162A2 (pt) | 2013-11-12 | 2015-09-08 | Dow Agrosciences Llc | processo para fluoração de compostos |
| 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） |
| 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 |
| KR102384529B1 (ko) * | 2016-07-07 | 2022-04-08 | 코르테바 애그리사이언스 엘엘씨 | 4-알콕시-3-(아실 또는 알킬)옥시피콜린아미드의 제조 방법 |
| KR102627532B1 (ko) * | 2018-02-02 | 2024-01-19 | 칸토 덴카 코교 가부시키가이샤 | 수소 및 불소 및/또는 염소를 함유한 부타디엔 골격을 갖는 화합물의 제조 방법 |
| BR112021005140A8 (pt) * | 2018-09-19 | 2021-06-29 | Corteva Agriscience Llc | preparação de análogos de halogênio de picloram |
| CN115298167A (zh) | 2020-03-18 | 2022-11-04 | 科迪华农业科技有限责任公司 | 6-芳基-4-氨基吡啶甲酸酯的改进合成 |
| US20230357155A1 (en) | 2020-03-18 | 2023-11-09 | Corteva Agriscience Llc | Improved synthesis of 4-amino-6-(heterocyclic)picolinates |
Family Cites Families (15)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3285925A (en) * | 1962-03-06 | 1966-11-15 | Dow Chemical Co | Amino-trichloropicolinic acid compounds |
| US3325272A (en) | 1965-06-23 | 1967-06-13 | Dow Chemical Co | Plant growth control methods and compositions |
| 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 |
| CN1042333C (zh) * | 1992-10-14 | 1999-03-03 | 美国氰胺公司 | 5,6－二取代－3－吡啶甲基卤化铵类化合物及其制备方法 |
| 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. |
| PT1246802E (pt) * | 2000-01-14 | 2007-06-18 | Dow Agrosciences Llc | 4-aminopicolinatos e sua utilização como herbicidas. |
| US6297197B1 (en) | 2000-01-14 | 2001-10-02 | Dow Agrosciences Llc | 4-aminopicolinates and their use as herbicides |
| 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 (uk) | 2003-04-02 | 2008-04-10 | Дау Агросайенсиз Ллс | 6-алкіл або алкеніл-4-амінопіколінати гербіцидна композиція, спосіб боротьби з небажаною рослинністю |
| WO2006062979A1 (en) * | 2004-12-06 | 2006-06-15 | E.I. Dupont De Nemours And Company | Herbicidal 6-cyclopropyl-substitute 4-aminopicolinic acid derivatives |
| CN102731382B (zh) * | 2006-01-13 | 2015-09-02 | 美国陶氏益农公司 | 6-(多取代芳基)-4-氨基吡啶甲酸酯及其作为除草剂的用途 |
| PL2332914T3 (pl) | 2007-10-02 | 2013-06-28 | Dow Agrosciences Llc | Podstawione kwasy 4-aminopikolinowe i ich zastosowanie jako herbicydów |
| 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 |
-
2012
- 2012-01-20 TW TW101102533A patent/TWI537252B/zh not_active IP Right Cessation
- 2012-01-24 RU RU2013139379/04A patent/RU2542985C1/ru not_active IP Right Cessation
- 2012-01-24 JP JP2013551279A patent/JP5781171B2/ja not_active Expired - Fee Related
- 2012-01-24 EP EP12739149.8A patent/EP2667712B1/en not_active Not-in-force
- 2012-01-24 PL PL12739149T patent/PL2667712T3/pl unknown
- 2012-01-24 SG SG2013056171A patent/SG192101A1/en unknown
- 2012-01-24 CA CA2825468A patent/CA2825468C/en not_active Expired - Fee Related
- 2012-01-24 KR KR1020147036124A patent/KR20150013334A/ko not_active Application Discontinuation
- 2012-01-24 MX MX2013008602A patent/MX338962B/es active IP Right Grant
- 2012-01-24 CN CN201280014129.7A patent/CN103458689B/zh not_active Expired - Fee Related
- 2012-01-24 US US13/356,686 patent/US8754231B2/en not_active Expired - Fee Related
- 2012-01-24 WO PCT/US2012/022289 patent/WO2012103045A1/en active Application Filing
- 2012-01-24 BR BR102012001643-5A patent/BR102012001643A2/pt not_active Application Discontinuation
- 2012-01-24 AU AU2012209281A patent/AU2012209281B2/en not_active Ceased
- 2012-01-24 UA UAA201310368A patent/UA109806C2/ru unknown
- 2012-01-24 BR BR112013018945A patent/BR112013018945A2/pt not_active Application Discontinuation
- 2012-01-24 KR KR1020137021997A patent/KR101537880B1/ko active IP Right Grant
- 2012-01-24 AR ARP120100232A patent/AR085020A1/es unknown
-
2013
- 2013-07-23 ZA ZA2013/05582A patent/ZA201305582B/en unknown
- 2013-07-24 IL IL227647A patent/IL227647B/en active IP Right Grant
- 2013-07-25 CO CO13175761A patent/CO6731129A2/es unknown
-
2014
- 2014-02-26 HK HK14101836.0A patent/HK1188684A1/zh not_active IP Right Cessation
- 2014-03-24 US US14/222,912 patent/US8993772B2/en not_active Expired - Fee Related
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