Process for the preparation of 3-(3-CHLORO-1H-pyrazol-1-yl)pyridine

• US 9,896,430 B2
• Filed: 04/12/2017
• Issued: 02/20/2018
• Est. Priority Date: 09/12/2014
• Status: Active Grant

• Current Assignee: Dow Agrosciences LLC (Corteva, Inc.)
• Original Assignee: Dow Agrosciences LLC (Corteva, Inc.)
• Inventors: Li, Xiaoyong, Yang, Qiang, Lorsbach, Beth
• Primary Examiner(s): Morris, Patricia L
• Application Number:
  US15/485,771
• Publication Number:
  US 20170217924A1
• Time in Patent Office: 314 Days
• Field of Search: 5462754
• CPC Class Codes: C07D 401/04 directly linked by a ring-member-to-ring-member bond

Abstract

This disclosure relates to the field of preparation of 3-(3-chloro-1H-pyrazol-1-yl)pyridine and intermediates therefrom. These intermediates are useful in the preparation of certain pesticides.

Claims

1. A process for preparing 3-(3-chloro-4-methyl-4,5-dihydro-1H-pyrazol-1-yl)pyridine (2)

2. The process of claim 1, wherein the chlorinating agent is selected from the group consisting of phosphoryl chloride, phosphorus pentachloride, and mixtures thereof.

3. The process of claim 2, wherein the chlorinating agent is phosphoryl chloride.

4. The process of claim 1, wherein the chlorinating agent is used in about a 1.1 fold to about a 10 fold excess compared to 4-methyl-1-(pyridin-3-yl)pyrazolidin-3-one.

5. The process of claim 1, wherein the organic solvent does not substantially react with the chlorinating reagent.

6. The process of claim 2, wherein the organic solvent does not substantially react with the chlorinating reagent.

7. The process of claim 3, wherein the organic solvent does not substantially react with the chlorinating reagent.

8. The process of claim 4, wherein the organic solvent does not substantially react with the chlorinating reagent.

9. The process of claim 1, wherein the organic solvent is a nitrile solvent.

10. The process of claim 2, wherein the organic solvent is a nitrile solvent.

11. The process of claim 3, wherein the organic solvent is a nitrile solvent.

12. The process of claim 4, wherein the organic solvent is a nitrile solvent.

13. The process of claim 1, wherein the organic solvent is acetonitrile.

14. The process of claim 2, wherein the organic solvent is acetonitrile.

15. The process of claim 3, wherein the organic solvent is acetonitrile.

16. The process of claim 4, wherein the organic solvent is acetonitrile.

17. The process of claim 1, wherein the temperature is about 75°

C.

18. The process of claim 3, wherein the temperature is about 75°

C.

19. The process of claim 11, wherein the temperature is about 75°

C.

20. The process of claim 15, wherein the temperature is about 75°

C.