Processes for the preparation of pesticidal compounds

• US 9,580,405 B2
• Filed: 05/27/2016
• Issued: 02/28/2017
• Est. Priority Date: 10/17/2013
• Status: Active Grant

• Current Assignee: Dow Agrosciences LLC (Corteva, Inc.)
• Original Assignee: Dow Agrosciences LLC (Corteva, Inc.)
• Inventors: Yang, Qiang, Lorsbach, Beth, Whiteker, Gregory, Roth, Gary, DeAmicis, Carl, Knueppel, Daniel I., Buysse, Ann M., Gray, Kaitlyn, Li, Xiaoyong, Muhuhi, Joseck M., Ross, Ronald Jr., Podhorez, David E., Zhang, Yu
• Primary Examiner(s): Morris, Patricia L
• Application Number:
  US15/166,784
• Publication Number:
  US 20160272615A1
• Time in Patent Office: 277 Days
• Field of Search: 546/275.4
• US Class Current: 1/1
• CPC Class Codes: A01N 43/56 1,2-Diazoles; Hydrogenated 1,2-diazoles
• CPC Class Codes: C07D 401/04 directly linked by a ring-member-to-ring-member bond

Abstract

The present application provides processes for making pesticidal compounds and compounds useful both as pesticides and in the making of pesticidal compounds.

Claims

1. A process for producing 3-(3-chloro-1H-pyrazol-1-yl)pyridine (5b) said process comprising

(a) reacting 3-hydrazinopyridine dihydrochloride with methyl 2-acetamidoacrylate to yield N-(3-oxo-1-(pyridin-3-yl)pyrazolidin-4-yl)acetamide;

and

(b) chlorinating/eliminating N-(3-oxo-1-(pyridin-3-yl)pyrazolidin-4-yl)acetamide to yield 3-(3-chloro-1H-pyrazol-1-yl)pyridine (5b)

2. The process of claim 1, wherein step (a) is carried out in the presence of sodium ethoxide.

3. The process of claim 1, wherein step (a) is carried out in the presence of ethanol.

4. The process of claim 3, wherein step (a) is carried out in the presence of sodium ethoxide.

5. The process of claim 1, wherein step (b) is carried out in the presence of POCl₃.

6. The process of claim 2, wherein step (b) is carried out in the presence of POCl₃.

7. The process of claim 3, wherein step (b) is carried out in the presence of POCl₃.

8. The process of claim 4, wherein step (b) is carried out in the presence of POCl₃.