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

• US 9,663,489 B2
• Filed: 07/28/2016
• Issued: 05/30/2017
• Est. Priority Date: 09/12/2014
• Status: Expired due to Fees

• Current Assignee: Dow Agrosciences LLC (Corteva, Inc.)
• Original Assignee: Dow Agrosciences LLC (Corteva, Inc.)
• Inventors: Lorsbach, Beth, Li, Xiaoyong, Yang, Qiang
• Primary Examiner(s): Morris, Patricia L
• Application Number:
  US15/222,473
• Publication Number:
  US 20160332986A1
• Time in Patent Office: 306 Days
• Field of Search: 5462761
• 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 4-methyl-1-(pyridin-3-yl)pyrazolidin-3-one (1)

2. The process of claim 1, wherein the (C₁-C₄) alkyl alcohol is selected from the group consisting of methanol, ethanol, propanol, butanol, and mixtures thereof.

3. The process of claim 2, wherein the (C₁-C₄) alkyl alcohol is ethanol.

4. The process of claim 1, wherein the alkali metal (C₁-C₄) alkoxide is selected from the group consisting of sodium methoxide, sodium ethoxide, and mixtures thereof.

5. The process of claim 1, wherein the (C₁-C₄) alkyl alcohol is ethanol and the alkali metal (C₁-C₄) alkoxide is sodium ethoxide.

6. The process of claim 2, wherein the alkali metal (C₁-C₄) alkoxide is selected from the group consisting of sodium methoxide, sodium ethoxide, and mixtures thereof.

7. The process of claim 6, wherein the alkyl methacrylate is used in about a 1.5 fold to about a 2 fold excess compared to 3-hydrazinopyridine•

dihydrochloride.

8. The process of claim 6, wherein the alkali metal (C₁-C₄) alkoxide is used about a 2 fold to about a 3 fold excess compared to 3-hydrazinopyridine•

dihydrochloride.

9. The process of claim 1, wherein the alkyl methacrylate is used in about a 1.5 fold to about a 2 fold excess compared to 3-hydrazinopyridine•

dihydrochloride.

10. The process of claim 4, wherein the alkali metal (C₁-C₄) alkoxide is used about a 2 fold to about a 3 fold excess compared to 3-hydrazinopyridine•

dihydrochloride.

11. The process of claim 4, wherein the alkali metal (C₁-C₄) alkoxide is used about a 2 fold to about a 3 fold excess compared to 3-hydrazinopyridin•

dihydrochloride.