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    Process for manufacturing 5-formyl-pyridine-2,3-dicarboxylic acid esters
    10.
    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。