2,4-Dichloro-5-(5-difluoromethoxy-1-methyl-1H-pyrazol-3-yl)nitrobenzene → 2,4-Dichloro-5-(5-difluoromethoxy-1-methyl-1H-pyrazol-3-yl)aniline

HRID 2180312Notes

Reaction equation

HRID 2180312 reaction equation
[Cl:1][C:2]1[CH:7]=[C:6]([Cl:8])[C:5]([C:9]2[CH:13]=[C:12]([O:14][CH:15]([F:17])[F:16])[N:11]([CH3:18])[N:10]=2)=[CH:4][C:3]=1[N+:19]([O-])=O.[H][H]>O1CCCC1.CO.[Ni]>[Cl:1][C:2]1[CH:7]=[C:6]([Cl:8])[C:5]([C:9]2[CH:13]=[C:12]([O:14][CH:15]([F:17])[F:16])[N:11]([CH3:18])[N:10]=2)=[CH:4][C:3]=1[NH2:19]

Participants

6

Reactant 2

HCID 224917282,4-Dichloro-5-(5-difluoromethoxy-1-methyl-1H-pyrazol-3-yl)nitrobenzeneHCID 178418361HCID 178418361, compound

Product 1

HCID 224917312,4-Dichloro-5-(5-difluoromethoxy-1-methyl-1H-pyrazol-3-yl)aniline

Reagents, catalysts & solvents 3

HCID 935NickelCatalystHCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

1.5 g (4.2 mmol) of 2,4-dichloro-5-(5-difluoromethoxy-1-methyl-1H-pyrazol-3-yl)nitrobenzene were dissolved in a mixture of 50 ml of tetrahydrofuran and 50 ml of methanol and admixed with 4 g of Raney nickel. The mixture was stirred at room temperature under a gage pressure of 0.3 bar of hydrogen for 4 h and then filtered through kieselguhr. The filtrate was dried using magnesium sulfate and then evaporated to dryness. This gave 1.3 g of the aniline.

Workup

  1. filtrationfiltered through kieselguhr
  2. customThe filtrate was dried
  3. customevaporated to dryness

Sources & evidence

ORD record
ord-5e17bcdaa0114531b45019aecc50d182
Source dataset
uspto-grants-2005_05
Patent number
US06888003B2

Reaction notes

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