Process for the preparation of 4-amino-5-fluoro-3-halo-6-(substituted)picolinates

• US 8,754,231 B2
• Filed: 01/24/2012
• Issued: 06/17/2014
• Est. Priority Date: 01/25/2011
• Status: Active Grant

• Current Assignee: Dow Agrosciences LLC (Corteva, Inc.)
• Original Assignee: Dow Agrosciences LLC (Corteva, Inc.)
• Inventors: Zhu, Yuanming, Whiteker, Gregory T., Renga, James M., Arndt, Kim E., Roth, Gary A., Podhorez, David E., West, Scott P.
• Primary Examiner(s): NORTHINGTON DAVIS, ZINNA
• Application Number:
  US13/356,686
• Publication Number:
  US 20120190859A1
• Time in Patent Office: 875 Days
• Field of Search: None
• US Class Current: 546/310
• CPC Class Codes: C07D 213/78 Carbon atoms having three bonds to hetero atoms, with at the most one bond to halogen, e.g. ester or nitrile radicals
• CPC Class Codes: C07D 213/79 Acids; Esters
• CPC Class Codes: C07D 213/803 Processes of preparation
• CPC Class Codes: C07D 213/81 Amides; Imides

Abstract

4-Amino-5-fluoro-3-halo-6-(substituted)picolinates are conveniently prepared from 4,5,6-trichloropicolinonitrile by a series of steps involving fluorine exchange, amination, halogen exchange, halogenation, nitrile hydrolysis, esterification, and transition metal assisted coupling.

Claims

1. A compound of the formula

2. The compound of claim 1 which is 4-amino-6-bromo-3-chloro-5-fluoropicolinamide.