RU2011154176A - Способ получения 6-(арил)-4-аминопиколинатов - Google Patents
Способ получения 6-(арил)-4-аминопиколинатов Download PDFInfo
- Publication number
- RU2011154176A RU2011154176A RU2011154176/04A RU2011154176A RU2011154176A RU 2011154176 A RU2011154176 A RU 2011154176A RU 2011154176/04 A RU2011154176/04 A RU 2011154176/04A RU 2011154176 A RU2011154176 A RU 2011154176A RU 2011154176 A RU2011154176 A RU 2011154176A
- Authority
- RU
- Russia
- Prior art keywords
- halogen
- aryl
- alkyl
- formula
- polar solvent
- Prior art date
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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
- C07D213/79—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
- C07D213/79—Acids; Esters
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D211/00—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings
- C07D211/04—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D211/80—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having two double bonds between ring members or between ring members and non-ring members
- C07D211/84—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having two double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms, with at the most one bond to halogen directly attached to ring carbon atoms
- C07D211/90—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Pyridine Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)
Abstract
1. Способ получения 6-(арил)-4-аминопиколината формулыгде Q представляет собой Cl или Br;R представляет собой С-Салкил; иW представляет собой H, F или Cl;X представляет собой H, F, Cl или С-Салкокси;Y представляет собой галоген; иZ представляет собой H или F;включающий нагревание эфира 3-галоген-6-(арил)-4-иминотетрагидропиколиновой кислоты формулы (I)где R представляет собой С-Салкил;Rпредставляет собой -OS(O)R, -OC(O)Rили -OC(O)OR;Rпредставляет собой С-Салкил или незамещенный или замещенный фенил;Q представляет собой Cl или Br; иW представляет собой H, F или Cl;X представляет собой H, F, Cl или С-Салкокси;Y представляет собой галоген; иZ представляет собой H или F;при температуре от 25°С до 150°С в присутствии полярного растворителя и выделение продукта.2. Способ по п.1, в котором полярным растворителем является С-Салкановой кислотой.3. Способ по п.1, в котором эфир 3-галоген-6-(арил)-4-иминотетрагидропиколиновой кислоты получают хлорированием или бромированием сульфонилированного, ацилированного или карбонатсодержащего оксима формулыгде W, X, Y, Z, R, Rи Rимеют значения, указанные выше, хлорирующим или бромирующим агентом.
Claims (3)
1. Способ получения 6-(арил)-4-аминопиколината формулы
где Q представляет собой Cl или Br;
R представляет собой С1-С4алкил; и
W представляет собой H, F или Cl;
X представляет собой H, F, Cl или С1-С4алкокси;
Y представляет собой галоген; и
Z представляет собой H или F;
включающий нагревание эфира 3-галоген-6-(арил)-4-иминотетрагидропиколиновой кислоты формулы (I)
где R представляет собой С1-С4алкил;
R1 представляет собой -OS(O)2R2, -OC(O)R2 или -OC(O)OR2;
R2 представляет собой С1-С4алкил или незамещенный или замещенный фенил;
Q представляет собой Cl или Br; и
W представляет собой H, F или Cl;
X представляет собой H, F, Cl или С1-С4алкокси;
Y представляет собой галоген; и
Z представляет собой H или F;
при температуре от 25°С до 150°С в присутствии полярного растворителя и выделение продукта.
2. Способ по п.1, в котором полярным растворителем является С1-С4алкановой кислотой.
3. Способ по п.1, в котором эфир 3-галоген-6-(арил)-4-иминотетрагидропиколиновой кислоты получают хлорированием или бромированием сульфонилированного, ацилированного или карбонатсодержащего оксима формулы
где W, X, Y, Z, R, R1 и R2 имеют значения, указанные выше, хлорирующим или бромирующим агентом.
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US18487409P | 2009-06-08 | 2009-06-08 | |
| US61/184,874 | 2009-06-08 | ||
| PCT/US2010/037670 WO2010144380A1 (en) | 2009-06-08 | 2010-06-08 | Process for the preparation of 6-(aryl)-4-aminopicolinates |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| RU2011154176A true RU2011154176A (ru) | 2013-07-20 |
| RU2525918C2 RU2525918C2 (ru) | 2014-08-20 |
Family
ID=42578185
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| RU2011154176/04A RU2525918C2 (ru) | 2009-06-08 | 2010-06-08 | Способ получения 6-арил-4-аминопиколинатов |
Country Status (7)
| Country | Link |
|---|---|
| US (1) | US8252938B2 (ru) |
| EP (1) | EP2440530B1 (ru) |
| JP (1) | JP5580888B2 (ru) |
| KR (1) | KR20120027015A (ru) |
| CN (2) | CN104788364A (ru) |
| RU (1) | RU2525918C2 (ru) |
| WO (1) | WO2010144380A1 (ru) |
Families Citing this family (10)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US8252938B2 (en) | 2009-06-08 | 2012-08-28 | Dow Agrosciences, Llc. | Process for the preparation of 6-(aryl)-4-aminopicolinates |
| 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） |
| TWI520943B (zh) * | 2011-01-25 | 2016-02-11 | 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（二） |
| TWI537252B (zh) * | 2011-01-25 | 2016-06-11 | 陶氏農業科學公司 | 用於製備４－胺基－５－氟－３－鹵素－６－（經取代之）吡啶甲酸酯的方法（一） |
| TWI529163B (zh) * | 2011-01-25 | 2016-04-11 | 陶氏農業科學公司 | 用於製備４－胺基－５－氟－３－鹵素－６－（經取代之）吡啶甲酸酯的方法 |
| GB201109309D0 (en) | 2011-06-02 | 2011-07-20 | Syngenta Ltd | Herbicidal compositions |
| BR102012016297A8 (pt) | 2011-06-30 | 2018-07-31 | Dow Agrosciences Llc | 3-alcóxi, tioalquila e amino-4-amino-6-(substituídos)picolinatos e sua aplicação como herbicidas |
| US8754110B2 (en) * | 2011-12-30 | 2014-06-17 | Dow Agrosciences, Llc. | Methods of producing methyl 4-amino-3-chloro-6-(4-chloro-2-fluoro-3-methoxyphenyl)pyridine-2-carboxylate |
| JP6239003B2 (ja) * | 2012-12-13 | 2017-11-29 | ダウ アグロサイエンシィズ エルエルシー | ４−アミノ−５−フルオロ−３−クロロ−６−（置換）ピコリネートの調製方法 |
| AR093946A1 (es) * | 2012-12-13 | 2015-07-01 | Dow Agrosciences Llc | Un proceso mejorado para el aislamiento del acido 4-amino-3-cloro-6-(4-cloro-2-fluor-3-metoxi-fenil)piridina-2-carboxilico |
Family Cites Families (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4304728A (en) | 1979-04-05 | 1981-12-08 | Lilly Industries Limited | 6-Substituted pyranone compounds and their use as pharmaceuticals |
| RU2220959C1 (ru) * | 2000-01-14 | 2004-01-10 | Дау Агросайенсиз Ллс | 4-аминопиколинаты и их применение в качестве гербицидов |
| 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 |
| AR059010A1 (es) | 2006-01-13 | 2008-03-05 | Dow Agrosciences Llc | 6-( aril polisustituido )-4- aminopicolinatos y su uso como herbicidas |
| US8252938B2 (en) | 2009-06-08 | 2012-08-28 | Dow Agrosciences, Llc. | Process for the preparation of 6-(aryl)-4-aminopicolinates |
-
2010
- 2010-06-07 US US12/795,184 patent/US8252938B2/en not_active Expired - Fee Related
- 2010-06-08 WO PCT/US2010/037670 patent/WO2010144380A1/en not_active Ceased
- 2010-06-08 KR KR1020117029245A patent/KR20120027015A/ko not_active Withdrawn
- 2010-06-08 CN CN201510140736.3A patent/CN104788364A/zh active Pending
- 2010-06-08 JP JP2012515027A patent/JP5580888B2/ja not_active Expired - Fee Related
- 2010-06-08 EP EP10727259.3A patent/EP2440530B1/en not_active Not-in-force
- 2010-06-08 RU RU2011154176/04A patent/RU2525918C2/ru not_active IP Right Cessation
- 2010-06-08 CN CN201080034936.6A patent/CN102803219B/zh not_active Expired - Fee Related
Also Published As
| Publication number | Publication date |
|---|---|
| KR20120027015A (ko) | 2012-03-20 |
| EP2440530A1 (en) | 2012-04-18 |
| CN102803219B (zh) | 2015-05-13 |
| CN102803219A (zh) | 2012-11-28 |
| CN104788364A (zh) | 2015-07-22 |
| WO2010144380A1 (en) | 2010-12-16 |
| US8252938B2 (en) | 2012-08-28 |
| EP2440530B1 (en) | 2013-07-24 |
| RU2525918C2 (ru) | 2014-08-20 |
| JP5580888B2 (ja) | 2014-08-27 |
| US20100311981A1 (en) | 2010-12-09 |
| JP2012529516A (ja) | 2012-11-22 |
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| Date | Code | Title | Description |
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| MM4A | The patent is invalid due to non-payment of fees |
Effective date: 20170609 |