Tetrahydrofuran → 3-(3-Fluoro-5-chloro-2-pyridyl)-4-amino-5difluoromethoxy-1-methyl-[1H]-pyrazole

HRID 1532581Notes

Reaction equation

HRID 1532581 reaction equation
[F:1][C:2]1[C:3]([C:9]2[C:13]([N+:14]([O-])=O)=[C:12]([O:17][CH:18]([F:20])[F:19])[N:11]([CH3:21])[N:10]=2)=[N:4][CH:5]=[C:6]([Cl:8])[CH:7]=1.O1CCCC1.[H][H]>[Ni].C(O)C>[F:1][C:2]1[C:3]([C:9]2[C:13]([NH2:14])=[C:12]([O:17][CH:18]([F:19])[F:20])[N:11]([CH3:21])[N:10]=2)=[N:4][CH:5]=[C:6]([Cl:8])[CH:7]=1

Participants

6

Reactant 3

HCID 8028TetrahydrofuranHCID 220135653-(3-Fluoro-5-chloro-2-pyridyl)-4-nitro-5-difluoromethoxy-1-methyl-[1H]-pyrazoleHCID 178418361HCID 178418361, compound

Product 1

HCID 220135593-(3-Fluoro-5-chloro-2-pyridyl)-4-amino-5difluoromethoxy-1-methyl-[1H]-pyrazole

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 702EthanolSolvent

Procedure

4.2 g of 3-(3-fluoro-5-chloro-2-pyridyl)-4-nitro-5-difluoromethoxy-1-methyl-[1H]-pyrazole (Example H47) are initially introduced into the reaction vessel together with 40 ml of tetrahydrofuran, and 5.8 g of Raney nickel in ethanol are added. Hydrogenation is carried out under normal pressure and at a temperature of 30-35° C. After uptake of 728 ml of hydrogen, the hydrogenation is interrupted and the reaction mixture is filtered over Hyflo. After removal of the solvent in vacuo, 3.15 g of the desired title compound are obtained as a brown solid of melting point 92-94° C.

Workup

  1. additionare added
  2. customis carried out under normal pressure and at a temperature of 30-35° C
  3. filtrationthe reaction mixture is filtered over Hyflo
  4. customAfter removal of the solvent in vacuo, 3.15 g of the desired title compound
  5. customare obtained as a brown solid of melting point 92-94° C.

Sources & evidence

ORD record
ord-5e58418e08774547a7d15f032556f7af
Source dataset
uspto-grants-2001_03
Patent number
US06204221B1

Reaction notes

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