Basf Se Corporation

Robert Leicht

Michael Rack

Michael Keil

Joachim Gebhardt

Frederik Menges

David Cortes

Helmut Zech

Rodney F Klima

Jochen Schroeder

Jochen Schröder

Stefan Orsten

Tony Yegerlehner

A process for manufacturing 5-chloromethyl-2,3-pyridine dicarboxylic acid anhydrides (I)   Compounds (I) are useful intermediates in the synthesis of herbicidal imidazolinones.

Process for manufacturing 5-chloromethyl-2,3-pyridine dicarboxylic acid anhydrides

A process for manufacturing 5,6-disubstituted-3-pyridylmethyl ammonium bromides (I), wherein 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 &#x3c;8, to obtain a 3-bromomethyl-5,6-disubstituted pyridine compound (III), wherein Y, Y, Z and Zhave the meanings given in formula (I), and

Process for manufacturing substituted 3-pyridylmethyl ammonium bromides

A process for manufacturing a 5-formyl-pyridine-2,3-dicarboxylic acid ester (I) wherein Z is hydrogen or halogen; Zis hydrogen, halogen, cyano or nitro and R, Rare independently C-C-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&#x2014;O&#x2014;N&#x2550;O (III) wherein Ris C-C-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 &#x2212;45 to 40&#xb0; C., to obtain an oxime compound (IV) where Z, Z, Rand Rare as in formula (I), and (ii) reacting oxime compound (IV) with an aliphatic C-C-aldehyde in the presence of a Lewis acid at a temperature in the range of from 0 to 100&#xb0; C. The compounds of formula (I) are useful intermediates in the synthesis of herbicidal imidazolinones, like imazamox. 

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

2-[(1-cyanopropyl)carbamoyl]-5-chloromethyl nicotinic acids of formula (I) where Z is hydrogen or halogen; Zis hydrogen, halogen, cyano or nitro; Ris C-Calkyl; Ris C-Calkyl, C-Ccycloalkyl or Rand R, when taken together with the atom to which they are attached, represent a C-Ccycloalkyl group optionally substituted with methyl, and Ris 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. 

2-[1-cyanopropyl)carbamoyl]-5-chloromethyl nicotinic acids and the use thereof in manufacturing herbicidal imidazolinones

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Hannibal, MO, United States of America

Robert Leicht