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    Process for manufacturing 5-formyl-pyridine-2,3-dicarboxylic acid esters
    2.
    发明授权
    Process for manufacturing 5-formyl-pyridine-2,3-dicarboxylic acid esters 有权
    5-甲酰基 - 吡啶-2,3-二羧酸酯的制备方法

    公开(公告)号：US08629279B2

    公开(公告)日：2014-01-14

    申请号：US13133013

    申请日：2009-12-07

    申请人： Michael Rack ,  Joachim Gebhardt ,  Frederik Menges ,  Michael Keil ,  Rodney F. Klima ,  David Cortes ,  Robert Leicht ,  Helmut Zech ,  Jochen Schröder

    发明人： Michael Rack ,  Joachim Gebhardt ,  Frederik Menges ,  Michael Keil ,  Rodney F. Klima ,  David Cortes ,  Robert Leicht ,  Helmut Zech ,  Jochen Schröder

    IPC分类号： C07D213/48 ,  C07D213/55

    CPC分类号： C07D213/80

    摘要： A process for manufacturing a 5-formyl-pyridine-2,3-dicarboxylic acid ester (I) wherein Z is hydrogen or halogen; Z1 is hydrogen, halogen, cyano or nitro and R1, R2 are independently C1-C10-alkyl, comprising the steps of (i) reacting a compound of formula (II), wherein the symbols are as in formula (I), with a nitrosation agent (III) R3—O—N═O (III) wherein R3 is C1-C8-alkyl, in the presence of an alkali metal or alkaline earth metal alcoholates or carbonates in a polar aprotic solvent at a temperature of from −45 to 40° C., to obtain an oxime compound (IV) where Z, Z1, R1 and R2 are as in formula (I), and (ii) reacting oxime compound (IV) with an aliphatic C1-C10-aldehyde in the presence of a Lewis acid at a temperature in the range of from 0 to 100° C. The compounds of formula (I) are useful intermediates in the synthesis of herbicidal imidazolinones, like imazamox.

    摘要翻译： 制备其中Z为氢或卤素的5-甲酰基 - 吡啶-2,3-二羧酸酯（I）的方法; Z1是氢，卤素，氰基或硝基，R1，R2独立地是C1-C10-烷基，包括以下步骤：（ⅰ）使符号如式（I）所示的式（ⅱ）化合物与式 在碱金属或碱土金属醇盐或碳酸盐存在下，在极性非质子溶剂中，温度为-45〜40℃的亚硝化剂（Ⅲ）R3-ON = O（Ⅲ）其中R3为C1-C8-烷基 ℃，得到其中Z，Z 1，R 1和R 2如式（I）中的肟化合物（Ⅳ），和（ⅱ）使肟化合物（Ⅳ）与脂族C 1 -C 10 - 醛在 在0至100℃的温度范围内的路易斯酸。式（I）化合物是合成除草咪唑啉酮如咪唑氧化物的有用中间体。

    Process for Manufacturing 5-Formyl-Pyridine-2,3-Dicarboxylic Acid Esters
    4.
    发明申请
    Process for Manufacturing 5-Formyl-Pyridine-2,3-Dicarboxylic Acid Esters 有权
    5-甲酰基 - 吡啶-2,3-二羧酸酯的制备方法

    公开(公告)号：US20110245505A1

    公开(公告)日：2011-10-06

    申请号：US13133013

    申请日：2009-12-07

    申请人： Michael Rack ,  Joachim Gebhardt ,  Frederik Menges ,  Michael Keil ,  Rodney F. Klima ,  David Cortes ,  Robert Leicht ,  Helmut Zech ,  Jochen Schröder

    发明人： Michael Rack ,  Joachim Gebhardt ,  Frederik Menges ,  Michael Keil ,  Rodney F. Klima ,  David Cortes ,  Robert Leicht ,  Helmut Zech ,  Jochen Schröder

    IPC分类号： C07D491/048 ,  C07D213/803 ,  C07D213/80 ,  C07D401/04

    CPC分类号： C07D213/80

    摘要： A process for manufacturing a 5-formyl-pyridine-2,3-dicarboxylic acid ester (I) wherein Z is hydrogen or halogen; Z1 is hydrogen, halogen, cyano or nitro and R1, R2 are independently C1-C10-alkyl, comprising the steps of (i) reacting a compound of formula (II), wherein the symbols are as in formula (I), with a nitrosation agent (III) R3—O—N═O (III) wherein R3 is C1-C8-alkyl, in the presence of an alkali metal or alkaline earth metal alcoholates or carbonates in a polar aprotic solvent at a temperature of from −45 to 40° C., to obtain an oxime compound (IV) where Z, Z1, R1 and R2 are as in formula (I), and (ii) reacting oxime compound (IV) with an aliphatic C1-C10-aldehyde in the presence of a Lewis acid at a temperature in the range of from 0 to 100° C. The compounds of formula (I) are useful intermediates in the synthesis of herbicidal imidazolinones, like imazamox.

    摘要翻译： 制备其中Z为氢或卤素的5-甲酰基 - 吡啶-2,3-二羧酸酯（I）的方法; Z1是氢，卤素，氰基或硝基，R1，R2独立地是C1-C10-烷基，包括以下步骤：（ⅰ）使符号如式（I）所示的式（ⅱ）化合物与式 在碱金属或碱土金属醇化物或碳酸盐存在下，在极性非质子溶剂中，温度为-45℃的亚硝化剂（III）R3-O-N = O（Ⅲ）其中R3为C1-C8-烷基 至40℃，得到其中Z，Z 1，R 1和R 2如式（I）中的肟化合物（Ⅳ），和（ⅱ）使肟化合物（Ⅳ）与脂族C 1 -C 10 - 醛在 在0至100℃的温度范围内存在路易斯酸。式（I）化合物是合成除草咪唑啉酮如咪唑氧化物的有用中间体。

    Process for manufacturing substituted 3-pyridylmethyl ammonium bromides
    5.
    发明授权
    Process for manufacturing substituted 3-pyridylmethyl ammonium bromides 有权
    制备取代的3-吡啶基甲基溴化铵的方法

    公开(公告)号：US09096570B2

    公开(公告)日：2015-08-04

    申请号：US13128787

    申请日：2009-11-13

    申请人： Joachim Gebhardt ,  Frederik Menges ,  Michael Rack ,  Michael Keil ,  Jochen Schroeder ,  Stefan Orsten ,  Helmut Zech ,  David Cortes ,  Robert Leicht ,  Tony Yegerlehner ,  Rodney F. Klima

    发明人： Joachim Gebhardt ,  Frederik Menges ,  Michael Rack ,  Michael Keil ,  Jochen Schroeder ,  Stefan Orsten ,  Helmut Zech ,  David Cortes ,  Robert Leicht ,  Tony Yegerlehner ,  Rodney F. Klima

    IPC分类号： C07D401/06 ,  C07D403/06 ,  C07D413/06 ,  C07D417/06 ,  C07D213/80 ,  C07D401/04

    CPC分类号： C07D401/04 ,  C07D213/80 ,  C07D401/06 ,  C07D403/06 ,  C07D413/06 ,  C07D417/06

    摘要： A process for manufacturing 5,6-disubstituted-3-pyridylmethyl ammonium bromides (I), wherein Q is a tertiary aliphatic or cyclic, saturated, partially unsaturated or aromatic amine; Z is hydrogen or halogen; Z1 is hydrogen, halogen, cyano or nitro; Y and Y1 are each independently OR1, NR1R2, or when taken together YY1 is —O—, —S— or NR3—; R1 and R2 are each independently hydrogen, C1-C4 alkyl optionally substituted with C1-C4 alkoxy or phenyl optionally substituted with one to three C1-C4 alkyl groups, C1-C4 alkoxy groups or halogen atoms, or phenyl optionally substituted with one to three C1-C4 alkyl groups, C1-C4 alkoxy groups or halogen atoms; R3 is hydrogen or C1-C4 alkyl; comprises the steps of (i) reacting a compound of formula (II), wherein the symbols have the meaning given in formula (I), with bromine in the presence of a radical initiator in a solvent mixture comprising an aqueous phase and an organic phase, where the organic phase comprises a solvent selected from 1,2-dichloroethane, chlorobenzene, 1,2-dichlorobenzene, 1,3-dichlorobenzene, 1,4-dichlorobenzene and tetrachloromethane, and where the pH-value of the aqueous phase is from 3 to

    摘要翻译： 制备5,6-二取代-3-吡啶基甲基溴化铵（I）的方法，其中Q是叔脂族或环状饱和的，部分不饱和的或芳族的胺; Z是氢或卤素; Z1是氢，卤素，氰基或硝基; Y和Y1各自独立地为OR 1，NR 1 R 2，或者当Y Y 1为-O - ， - S-或NR 3 - 时。 R 1和R 2各自独立地为氢，任选被C 1 -C 4烷氧基取代的C 1 -C 4烷基或任选被一至三个C 1 -C 4烷基，C 1 -C 4烷氧基或卤素原子取代的苯基，或任选被一至三个 C1-C4烷基，C1-C4烷氧基或卤原子; R3是氢或C1-C4烷基; 包括以下步骤：（i）在自由基引发剂存在下，将包含式（I）中给出的符号的式（II）化合物与溴在含水相和有机相的溶剂混合物中反应， 其中有机相包含选自1,2-二氯乙烷，氯苯，1,2-二氯苯，1,3-二氯苯，1,4-二氯苯和四氯甲烷的溶剂，其中水相的pH值来自 3至<8，得到3-溴甲基-5,6-二取代的吡啶化合物（III），其中Y，Y 1，Z和Z 1具有式（I）中给出的含义，和（ⅱ）使溴化合物 式（III）与叔胺碱Q在溶剂中在约0℃至100℃的温度范围内

    Process for Manufacturing Substituted 3-pyridylmethyl Ammonium Bromides
    7.
    发明申请
    Process for Manufacturing Substituted 3-pyridylmethyl Ammonium Bromides 有权
    制备取代的3-吡啶基甲基溴化铵的方法

    公开(公告)号：US20110224433A1

    公开(公告)日：2011-09-15

    申请号：US13128787

    申请日：2009-11-13

    申请人： Joachim Gebhardt ,  Frederik Menges ,  Michael Rack ,  Michael Keil ,  Jochen Schroeder ,  Stefan Orsten ,  Helmut Zech ,  David Cortes ,  Robert Leicht ,  Tony Yegerlehner ,  Rodney F. Klima

    发明人： Joachim Gebhardt ,  Frederik Menges ,  Michael Rack ,  Michael Keil ,  Jochen Schroeder ,  Stefan Orsten ,  Helmut Zech ,  David Cortes ,  Robert Leicht ,  Tony Yegerlehner ,  Rodney F. Klima

    IPC分类号： C07D251/00 ,  C07D213/80 ,  C07D237/00 ,  C07D241/00 ,  C07D401/04

    CPC分类号： C07D401/04 ,  C07D213/80 ,  C07D401/06 ,  C07D403/06 ,  C07D413/06 ,  C07D417/06

    摘要： A process for manufacturing 5,6-disubstituted-3-pyridylmethyl ammonium bromides (I), wherein Q is a tertiary aliphatic or cyclic, saturated, partially unsaturated or aromatic amine; Z is hydrogen or halogen; Z1 is hydrogen, halogen, cyano or nitro; Y and Y1 are each independently OR1, NR1R2, or when taken together YY1 is —O—, —S— or NR3—; R1 and R2 are each independently hydrogen, C1-C4 alkyl optionally substituted with C1-C4 alkoxy or phenyl optionally substituted with one to three C1-C4 alkyl groups, C1-C4 alkoxy groups or halogen atoms, or phenyl optionally substituted with one to three C1-C4 alkyl groups, C1-C4 alkoxy groups or halogen atoms; R3 is hydrogen or C1-C4 alkyl; comprises the steps of (i) reacting a compound of formula (II), wherein the symbols have the meaning given in formula (I), with bromine in the presence of a radical initiator in a solvent mixture comprising an aqueous phase and an organic phase, where the organic phase comprises a solvent selected from 1,2-dichloroethane, chlorobenzene, 1,2-dichlorobenzene, 1,3-dichlorobenzene, 1,4-dichlorobenzene and tetrachloromethane, and where the pH-value of the aqueous phase is from 3 to

    摘要翻译： 制备5,6-二取代-3-吡啶基甲基溴化铵（I）的方法，其中Q是叔脂族或环状饱和的，部分不饱和的或芳族的胺; Z是氢或卤素; Z1是氢，卤素，氰基或硝基; Y和Y1各自独立地为OR 1，NR 1 R 2，或者当Y Y 1为-O - ， - S-或NR 3 - 时。 R 1和R 2各自独立地为氢，任选被C 1 -C 4烷氧基取代的C 1 -C 4烷基或任选被一至三个C 1 -C 4烷基，C 1 -C 4烷氧基或卤素原子取代的苯基，或任选被一至三个 C1-C4烷基，C1-C4烷氧基或卤原子; R3是氢或C1-C4烷基; 包括以下步骤：（i）在自由基引发剂存在下，将包含式（I）中给出的符号的式（II）化合物与溴在含水相和有机相的溶剂混合物中反应， 其中有机相包含选自1,2-二氯乙烷，氯苯，1,2-二氯苯，1,3-二氯苯，1,4-二氯苯和四氯甲烷的溶剂，其中水相的pH值来自 3至<8，得到3-溴甲基-5,6-二取代的吡啶化合物（III），其中Y，Y 1，Z和Z 1具有式（I）中给出的含义，和（ⅱ）使溴化合物 式（III）与叔胺碱Q在溶剂中在约0℃至100℃的温度范围内

    Process for Manufacturing Substituted 5-Methoxymethylpyridine-2,3-Dicarboxylic Acid Derivatives
    9.
    发明申请
    Process for Manufacturing Substituted 5-Methoxymethylpyridine-2,3-Dicarboxylic Acid Derivatives 审中-公开
    制备取代的5-甲氧基甲基吡啶-2,3-二羧酸衍生物的方法

    公开(公告)号：US20110245506A1

    公开(公告)日：2011-10-06

    申请号：US13133008

    申请日：2009-12-07

    申请人： David Cortes

    发明人： David Cortes

    IPC分类号： C07D213/803 ,  C07D213/84 ,  C07D401/04

    CPC分类号： C07D213/84 ,  C07D213/80 ,  C07D401/04

    摘要： A process for manufacturing a 2,3-disubstituted-5-methoxymethylpyridine of formula (I), where Z is H or halogen; Z1 is H, halogen, CN or NO2; Y2 is OM, and M is an alkali metal or an alkaline earth metal, comprises the step of: (i) reacting a compound of formula (II) where Q is a tertiary aliphatic or cyclic, saturated, partially unsaturated or aromatic amine; Z is H or halogen; Z1 is H, halogen, CN or NO2; Y1 and Y2 are each independently OR1, NR1R2, or when taken together Y1Y2 is —O—, —S— or —NR3—; R1 and R2 are each independently H, C1-C4 alkyl optionally substituted with C1-C1 alkoxy or phenyl optionally substituted with one to three C1-C4 alkyl groups, C1-C4 alkoxy groups or halogen atoms, or phenyl optionally substituted with one to three C1-C4 alkyl groups, C1-C4 alkoxy groups or halogen atoms; R3 is H or C1-C4 alkyl, in a methanol/H2O mixture, comprising at least 20% by weight H2O (based on the sum of water and bromide (II)), with a base comprising MOCH3 and/or MOH, where M is alkali metal or alkaline earth metal, under pressure in a closed vessel at a temperature of from 75 to 110° C. Compounds of formula (I) are useful intermediates in the synthesis of herbicidal imidazolinones, like imazamox.

    摘要翻译： 制备式（I）的2,3-二取代-5-甲氧基甲基吡啶的方法，其中Z是H或卤素; Z1是H，卤素，CN或NO2; Y2是OM，M是碱金属或碱土金属，包括以下步骤：（i）使Q为叔脂族或环状饱和，部分不饱和或芳族胺的式（II）化合物反应; Z是H或卤素; Z1是H，卤素，CN或NO2; Y1和Y2各自独立地为OR1，NR1R2，或者当Y1Y2为-O - ， - S-或-NR3-时; R 1和R 2各自独立地为H，任选地被C 1 -C 1烷氧基取代的C 1 -C 4烷基或任选被一至三个C 1 -C 4烷基，C 1 -C 4烷氧基或卤素原子取代的苯基，或任选被一至三个 C1-C4烷基，C1-C4烷氧基或卤原子; 在甲醇/ H 2 O混合物中，R 3是H或C 1 -C 4烷基，其包含至少20重量％的H 2 O（基于水和溴（II）的总和））与包含MOCH 3和/或MOH的碱，其中M 是碱金属或碱土金属，在密封容器中在75〜110℃的温度下进行加压。式（I）化合物是合成除草咪唑啉酮类似咪唑氧化物的有用中间体。