Abstract:
A process for manufacturing 5-chloromethyl-2,3-pyridine dicarboxylic acid anhydrides (I) wherein Z is hydrogen or halogen; Z 1 is hydrogen, halogen, cyano or nitro; comprising the steps of (i) reacting a compound of formula (II), wherein the symbols have the meaning given in formula (I), with a chlorinating agent, optionally in the presence of a radical initiator in a solvent selected from halogenated hydrocarbons, and (ii) crystallizing the compound (I) formed in step (i) from a solvent selected from chlorobenzene, 1,2-dichlorobenzene, 1,3-dichlorobenzene, 1,4-dichlorobenzene, dichloroethane, trichloromethane, dichloromethane, toluene, xylenes, ethyl acetate, methyl tert.-butyl ether, and mixtures thereof. Compounds (I) are useful intermediates in the synthesis of herbicidal imidazolinones.
Abstract translation:一种制备其中Z是氢或卤素的5-氯甲基-2,3-吡啶二羧酸酸酐(Ⅰ)的方法; Z 1是氢,卤素,氰基或硝基; 包括以下步骤:(i)使式(II)化合物(其中符号具有式(I)中给出的含义)与氯化剂任选在自由基引发剂存在下在选自卤代烃, (ii)使步骤(i)中形成的化合物(I)从选自氯苯,1,2-二氯苯,1,3-二氯苯,1,4-二氯苯,二氯乙烷,三氯甲烷,二氯甲烷,甲苯,二甲苯 ,乙酸乙酯,甲基叔丁基醚及其混合物。 化合物(I)是合成除草咪唑啉酮的有用中间体。
Abstract:
A process for manufacturing a 5-formyl-pyridine-2,3-dicarboxylic acid ester (I) wherein Z is hydrogen or halogen; Z 1 is hydrogen, halogen, cyano or nitro and R 1 , R 2 are independently C 1 -C 10 -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) R 3 -O-N=O (III) wherein R 3 is C 1 -C 8 -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, Z 1 , R 1 and R 2 are as in formula (I), and (ii) reacting oxime compound (IV) with an aliphatic C 1 -C 10 -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.
Abstract:
2-[(1-cyanopropyl)carbamoyl]-5-chloromethyl nicotinic acids of formula (I) where Z is hydrogen or halogen; Z 1 is hydrogen, halogen, cyano or nitro; R 1 is C 1 -C 4 alkyl; R 2 is C 1 -C 4 alkyl, C 3 -C 6 cycloalkyl or R 1 and R 2 , when taken together with the atom to which they are attached, represent a C 3 -C 6 cycloalkyl group optionally substituted with methyl, and R 3 is hydrogen or a cation preferably selected from the group consisting of alkali metals, alkaline earth metals, manganese, copper, iron, zinc, cobalt, lead, silver, nickel, ammonium and organic ammonium; are useful intermediates for the synthesis of herbicidal imidazolinones.