AR074511A1 - Proceso para la fabricacion de derivados del acido 5-metoximetilpiridin-2,3-dicarboxilico sustituido - Google Patents
Proceso para la fabricacion de derivados del acido 5-metoximetilpiridin-2,3-dicarboxilico sustituidoInfo
- Publication number
- AR074511A1 AR074511A1 ARP090104745A ARP090104745A AR074511A1 AR 074511 A1 AR074511 A1 AR 074511A1 AR P090104745 A ARP090104745 A AR P090104745A AR P090104745 A ARP090104745 A AR P090104745A AR 074511 A1 AR074511 A1 AR 074511A1
- Authority
- AR
- Argentina
- Prior art keywords
- formula
- alkyl
- halogen
- optionally substituted
- alkoxy
- Prior art date
Links
- 238000004519 manufacturing process Methods 0.000 title abstract 3
- 238000000034 method Methods 0.000 title abstract 2
- 239000002253 acid Substances 0.000 title 1
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 abstract 6
- 229910052736 halogen Inorganic materials 0.000 abstract 6
- 150000002367 halogens Chemical class 0.000 abstract 6
- 150000001875 compounds Chemical class 0.000 abstract 5
- 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 abstract 4
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 abstract 4
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 abstract 4
- 125000006274 (C1-C3)alkoxy group Chemical group 0.000 abstract 3
- 125000000229 (C1-C4)alkoxy group Chemical group 0.000 abstract 3
- -1 2,3-disubstituted-5-methoxymethylpyridine Chemical class 0.000 abstract 3
- 125000005843 halogen group Chemical group 0.000 abstract 3
- 230000002363 herbicidal effect Effects 0.000 abstract 3
- 229910052783 alkali metal Inorganic materials 0.000 abstract 2
- 150000001340 alkali metals Chemical class 0.000 abstract 2
- 229910052784 alkaline earth metal Inorganic materials 0.000 abstract 2
- 150000001342 alkaline earth metals Chemical class 0.000 abstract 2
- 125000004453 alkoxycarbonyl group Chemical group 0.000 abstract 2
- 125000004400 (C1-C12) alkyl group Chemical group 0.000 abstract 1
- 125000006273 (C1-C3) alkyl group Chemical group 0.000 abstract 1
- NUPJIGQFXCQJBK-UHFFFAOYSA-N 2-(4-isopropyl-4-methyl-5-oxo-4,5-dihydro-1H-imidazol-2-yl)-5-(methoxymethyl)nicotinic acid Chemical compound OC(=O)C1=CC(COC)=CN=C1C1=NC(C)(C(C)C)C(=O)N1 NUPJIGQFXCQJBK-UHFFFAOYSA-N 0.000 abstract 1
- CAAMSDWKXXPUJR-UHFFFAOYSA-N 3,5-dihydro-4H-imidazol-4-one Chemical class O=C1CNC=N1 CAAMSDWKXXPUJR-UHFFFAOYSA-N 0.000 abstract 1
- CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 abstract 1
- 239000005566 Imazamox Substances 0.000 abstract 1
- 125000001931 aliphatic group Chemical group 0.000 abstract 1
- 125000003342 alkenyl group Chemical group 0.000 abstract 1
- 125000005036 alkoxyphenyl group Chemical group 0.000 abstract 1
- 125000005210 alkyl ammonium group Chemical group 0.000 abstract 1
- 125000000217 alkyl group Chemical group 0.000 abstract 1
- 125000005037 alkyl phenyl group Chemical group 0.000 abstract 1
- 150000004982 aromatic amines Chemical class 0.000 abstract 1
- 125000004429 atom Chemical group 0.000 abstract 1
- 239000002585 base Substances 0.000 abstract 1
- 230000015572 biosynthetic process Effects 0.000 abstract 1
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 abstract 1
- 150000001768 cations Chemical class 0.000 abstract 1
- 125000004093 cyano group Chemical group *C#N 0.000 abstract 1
- 125000004122 cyclic group Chemical group 0.000 abstract 1
- 125000005059 halophenyl group Chemical group 0.000 abstract 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 abstract 1
- 239000000543 intermediate Substances 0.000 abstract 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 abstract 1
- 239000000203 mixture Substances 0.000 abstract 1
- 125000006501 nitrophenyl group Chemical group 0.000 abstract 1
- 229920006395 saturated elastomer Polymers 0.000 abstract 1
- 238000003786 synthesis reaction Methods 0.000 abstract 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 abstract 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
- C07D213/78—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
- C07D213/78—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
- C07D213/80—Acids; Esters in position 3
-
- 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
- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
- C07D401/04—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings directly linked by a ring-member-to-ring-member bond
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Plural Heterocyclic Compounds (AREA)
- Pyridine Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
Abstract
Un proceso para la fabricación de 2,3-disustituida-5-metoximetilpiridina de la fórmula (1), en donde Z es H o halógeno; Z1 es H, halógeno, CN o NO2, Y2 es OM, y M es un metal alcalino o un metal alcalinotérreo que comprende la etapa de; (i) hacer reaccionar un compuesto de la fórmula (2) en donde Q es una amina terciaria, alifática o cíclica, saturada, parcialmente insaturada o aromática; Z es H o halógeno; Z1 es H, halógeno, CN o NO2,Y1 y Y2 son cada uno, independientemente. OR1, NR1R2 o, cuando se toman en forma conjunta, Y1Y2 es -O-, -S- o -NR3-; R1 y R2 son cada uno independientemente, H, alquilo C1-4 opcionalmente sustituido con alcoxi C1-4 o fenilo opcionalmente sustituido con uno a tres grupos alquilo C1-4, alcoxi C1-4 o átomos de halógeno, o fenilo opcionalmente sustituido con uno a tres grupos alquilo C1-4, alcoxi C1-4 o átomos de halógeno; R3 es H o alquilo C1-4; en una mezcla de metanol/H2O, que comprende por lo menos 20% en peso de H2O (sobre la base de la suma de agua y bromuro (ii)), con una base que comprende MOCH3, y/o MOH, donde M es metal alcalino o metal alcalinotérreo, bajo presión en un recipiente cerrado a una temperatura de 75 a 100sC. Los compuestos de la fórmula (1) son intermediarios útiles en la síntesis de imidazolinonas herbicidas, como imazamox. Reivindicación 13: Un proceso para preparar un compuesto de imidazolinona herbicida de la fórmula (3) en done Z, Z1 son como se definen en la fórmula (1) de la reivindicación 1; R4 es alquilo C1-4; R5 alquilo C1-4, cicloalquilo C3-6 o R4 y R5, cuando se los toma junto con el átomo al cual están unidos, representan un grupo cicloalquilo C3-6 opcionalmente sustituido con metilo y R6 es H, un grupo de la fórmula -N=C (alquilo inferior)2, alquilo C1-12 opcionalmente sustituido con uno de los siguientes grupos: alcoxi C1-3, halógeno, hidroxilo, cicloalquilo C3-6, benciloxi, furilo, fenilo, halofenilo, alquilfenilo inferior, alcoxifenilo inferior, nitrofenilo, carboxilo, alcoxicarbonilo inferior, ciano o tri alquilamonio inferior, alquenilo C3-12 opcionalmente sustituido con uno de los siguientes grupos: alcoxi C1-3, fenilo, halógeno o alcoxicarbonilo inferior o con dos grupos alcoxi C1-3 o dos grupos halógeno, cicloalquilo C3-6 opcionalmente sustituido con uno o dos grupos alquilo C1-3; o un catión; caracterizado porque comprende las etapas de: (i) preparar un compuesto de fórmula (1) de acuerdo con una de las reivindicaciones 1 a 12, (ii) convertir el compuesto de la fórmula (1) en un compuesto herbicida de la fórmula (3).
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US12061308P | 2008-12-08 | 2008-12-08 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| AR074511A1 true AR074511A1 (es) | 2011-01-19 |
Family
ID=41510661
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| ARP090104745A AR074511A1 (es) | 2008-12-08 | 2009-12-07 | Proceso para la fabricacion de derivados del acido 5-metoximetilpiridin-2,3-dicarboxilico sustituido |
Country Status (16)
| Country | Link |
|---|---|
| US (2) | US20110245506A1 (es) |
| EP (1) | EP2373623B1 (es) |
| JP (1) | JP5670343B2 (es) |
| CN (2) | CN107235895A (es) |
| AR (1) | AR074511A1 (es) |
| AU (1) | AU2009326095B2 (es) |
| BR (1) | BRPI0923297B1 (es) |
| CA (1) | CA2744368C (es) |
| DK (1) | DK2373623T3 (es) |
| IL (1) | IL212991A (es) |
| MX (1) | MX2011005827A (es) |
| RU (1) | RU2549894C2 (es) |
| TW (1) | TWI506019B (es) |
| UA (1) | UA101712C2 (es) |
| UY (1) | UY32309A (es) |
| WO (1) | WO2010066669A1 (es) |
Families Citing this family (12)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN105777623A (zh) * | 2016-02-29 | 2016-07-20 | 北京颖泰嘉和生物科技股份有限公司 | 一种吡啶侧链甲基季铵盐类化合物的制备方法 |
| WO2018091964A1 (en) | 2016-11-21 | 2018-05-24 | Adama Agan Ltd. | Process for preparing methoxy methyl pyridine dicarboxylate |
| CN107033067A (zh) * | 2017-06-25 | 2017-08-11 | 刘瑞海 | 一种2‑甲氧基甲基吡啶的合成方法 |
| CN107216286B (zh) * | 2017-06-27 | 2020-03-31 | 江苏省农用激素工程技术研究中心有限公司 | 5-溴甲基-2,3-吡啶二甲酸二甲酯的制备方法 |
| CN109467531A (zh) * | 2017-09-08 | 2019-03-15 | 沈阳科创化学品有限公司 | 一种取代吡啶二羧酸衍生物的制备方法 |
| RU2707043C1 (ru) * | 2019-03-25 | 2019-11-21 | Акционерное общество "Щелково Агрохим" | Способ получения гербицида имазамокса |
| EP3782985A1 (en) | 2019-08-19 | 2021-02-24 | BASF Agrochemical Products B.V. | Process for manufacturing 5-methoxymethylpyridine-2,3-dicarboxylic acid derivatives |
| CN113061125B (zh) * | 2019-12-13 | 2022-11-01 | 沈阳中化农药化工研发有限公司 | 一种咪唑啉酮化合物的制备方法 |
| CN111004174A (zh) * | 2019-12-24 | 2020-04-14 | 沈阳化工研究院有限公司 | 一种紫外光催化制备5-溴甲基-2，3-吡啶二甲酸二甲酯的方法 |
| CN113968814A (zh) * | 2020-07-22 | 2022-01-25 | 帕潘纳(北京)科技有限公司 | 一种制备5-溴甲基-2,3-吡啶羧酸二甲酯的方法 |
| CN114933561A (zh) * | 2022-05-09 | 2022-08-23 | 沈阳万菱生物技术有限公司 | 一种5-取代-2,3-吡啶二羧酸酯化合物及其季铵盐的制备方法 |
| CN116715626A (zh) * | 2023-06-05 | 2023-09-08 | 山东先达农化股份有限公司 | 一种制备咪唑啉酮化合物(i)的中间体及其应用 |
Family Cites Families (13)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4460776A (en) * | 1982-05-25 | 1984-07-17 | American Cyanamid Company | Process for the preparation of 6-substituted-2,3-pyridinedicarboxylic acid diesters |
| GB8605868D0 (en) * | 1986-03-10 | 1986-04-16 | Shell Int Research | Preparation of heterocyclic compounds |
| GB2192877A (en) * | 1986-07-22 | 1988-01-27 | Shell Int Research | Herbicidal imidazolinyl compounds |
| EP0322616A3 (en) | 1987-12-31 | 1989-10-18 | American Cyanamid Company | Novel 5(and/or 6)substituted 2-(2-imidazolin-2-yl)nicotinic acids, esters and salts, useful as herbicidal agents and nivel intermediates for the preparation of said nicotinic acids, esters and salts |
| EP0434965B1 (en) * | 1989-12-27 | 1998-05-20 | American Cyanamid Company | Alkyl esters of 5-heterocyclic-pyridine-2,3-dicarboxylic acids and 5-heterocyclic 2-(2-imidazolin-2-yl) pyridines and methods for preparation thereof |
| US5177266A (en) | 1991-12-20 | 1993-01-05 | American Cyanamid Company | Proccess for the manufacture of 2-alkoxymethylacrolein |
| US5288866A (en) * | 1991-12-20 | 1994-02-22 | American Cyanamid Company | 5,6-disubstituted-3-pyridylmethyl ammonium halide compounds useful for the preparation of 5- (substituted methyl)-2,3-pyridinedicarboxylic acids |
| US5250694A (en) * | 1992-08-26 | 1993-10-05 | American Cyanamid Company | Process for the preparation of 2,3-pyridine-dicarboxylic acids from 3-(2-imidazolin-2-yl)picolinic acids |
| 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 |
| JP3963499B2 (ja) * | 1995-06-05 | 2007-08-22 | ワイス・ホールディングズ・コーポレイション | ５−（アルコキシメチル）ピリジン−２，３−ジカルボン酸塩の改良された製造方法 |
| US5892050A (en) | 1998-01-28 | 1999-04-06 | American Cyanamid Company | Process for the preparation of pyridine dicarboxylate derivatives |
| US8826226B2 (en) * | 2008-11-05 | 2014-09-02 | Google Inc. | Custom language models |
| CN101739539B (zh) * | 2008-11-06 | 2011-09-21 | 国民技术股份有限公司 | 采用自动跳频抗读卡冲突的方法 |
-
2009
- 2009-11-20 TW TW098139547A patent/TWI506019B/zh not_active IP Right Cessation
- 2009-12-07 RU RU2011127905/04A patent/RU2549894C2/ru active
- 2009-12-07 CA CA2744368A patent/CA2744368C/en active Active
- 2009-12-07 DK DK09764529.5T patent/DK2373623T3/en active
- 2009-12-07 MX MX2011005827A patent/MX2011005827A/es active IP Right Grant
- 2009-12-07 JP JP2011539047A patent/JP5670343B2/ja active Active
- 2009-12-07 WO PCT/EP2009/066496 patent/WO2010066669A1/en not_active Ceased
- 2009-12-07 AU AU2009326095A patent/AU2009326095B2/en active Active
- 2009-12-07 AR ARP090104745A patent/AR074511A1/es active IP Right Grant
- 2009-12-07 CN CN201710531422.5A patent/CN107235895A/zh active Pending
- 2009-12-07 CN CN200980148945.5A patent/CN102245575B/zh active Active
- 2009-12-07 EP EP09764529.5A patent/EP2373623B1/en active Active
- 2009-12-07 US US13/133,008 patent/US20110245506A1/en not_active Abandoned
- 2009-12-07 BR BRPI0923297-4A patent/BRPI0923297B1/pt active IP Right Grant
- 2009-12-07 UA UAA201108455A patent/UA101712C2/ru unknown
- 2009-12-08 UY UY0001032309A patent/UY32309A/es unknown
-
2011
- 2011-05-19 IL IL212991A patent/IL212991A/en active IP Right Grant
-
2017
- 2017-01-19 US US15/410,214 patent/US10858320B2/en active Active
Also Published As
| Publication number | Publication date |
|---|---|
| DK2373623T3 (en) | 2017-07-10 |
| CA2744368A1 (en) | 2010-06-17 |
| EP2373623A1 (en) | 2011-10-12 |
| CN107235895A (zh) | 2017-10-10 |
| EP2373623B1 (en) | 2017-03-29 |
| US20110245506A1 (en) | 2011-10-06 |
| UY32309A (es) | 2010-06-30 |
| JP2012510978A (ja) | 2012-05-17 |
| WO2010066669A1 (en) | 2010-06-17 |
| MX2011005827A (es) | 2011-06-21 |
| TWI506019B (zh) | 2015-11-01 |
| AU2009326095A1 (en) | 2011-06-30 |
| JP5670343B2 (ja) | 2015-02-18 |
| AU2009326095B2 (en) | 2016-02-11 |
| CN102245575B (zh) | 2017-07-28 |
| IL212991A0 (en) | 2011-07-31 |
| UA101712C2 (ru) | 2013-04-25 |
| BRPI0923297A2 (pt) | 2015-07-28 |
| CN102245575A (zh) | 2011-11-16 |
| IL212991A (en) | 2013-08-29 |
| CA2744368C (en) | 2017-04-04 |
| US20170226060A1 (en) | 2017-08-10 |
| RU2549894C2 (ru) | 2015-05-10 |
| BRPI0923297B1 (pt) | 2018-03-06 |
| US10858320B2 (en) | 2020-12-08 |
| TW201035052A (en) | 2010-10-01 |
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