4-chloro-3-(2-fluoro-5-methoxy-4-nitrophenyl)-1-methyl-5-(trifluoromethyl)-1H-pyrazole → 4-chloro-3-(4-amino-2-fluoro-5-methoxyphenyl)-1-methyl-5-(trifluoromethyl)-1H-pyrazole

HRID 1440134Notes

Reaction equation

HRID 1440134 reaction equation
[Cl:1][C:2]1[C:3]([C:12]2[CH:17]=[C:16]([O:18][CH3:19])[C:15]([N+:20]([O-])=O)=[CH:14][C:13]=2[F:23])=[N:4][N:5]([CH3:11])[C:6]=1[C:7]([F:10])([F:9])[F:8]>C(O)(=O)C.[Fe]>[Cl:1][C:2]1[C:3]([C:12]2[CH:17]=[C:16]([O:18][CH3:19])[C:15]([NH2:20])=[CH:14][C:13]=2[F:23])=[N:4][N:5]([CH3:11])[C:6]=1[C:7]([F:10])([F:8])[F:9]

Participants

4

Reactant 1

HCID 152785724-chloro-3-(2-fluoro-5-methoxy-4-nitrophenyl)-1-methyl-5-(trifluoromethyl)-1H-pyrazole

Product 1

HCID 194367624-chloro-3-(4-amino-2-fluoro-5-methoxyphenyl)-1-methyl-5-(trifluoromethyl)-1H-pyrazoleYield 95.5%

Reagents, catalysts & solvents 2

HCID 23925IronCatalyst2×HCID 176Acetic AcidSolvent

Procedure

To a solution of 4.05 g of 4-chloro-3-(2-fluoro-5-methoxy-4-nitrophenyl)-1-methyl-5-(trifluoromethyl)-1H-pyrazole in 50 ml of acetic acid was added 1.39 g (0.0249 mol) of iron powder. The reaction mixture was heated near reflux for 2 hours, treated with 1.39 g of iron powder, and heated at near reflux for another hour. After cooling, concentrating and chromatography, 3.54 g of 4-chloro-3-(4-amino-2-fluoro-5-methoxyphenyl)-1-methyl-5-(trifluoromethyl)-1H-pyrazole was isolated.

Workup

  1. temperatureThe reaction mixture was heated
  2. temperaturenear reflux for 2 hours
  3. temperatureheated
  4. temperatureat near reflux for another hour
  5. temperatureAfter cooling
  6. concentrationconcentrating

Sources & evidence

ORD record
ord-4ce01003d8dd4771a8503439a06c1705
Source dataset
uspto-grants-1996_03
Patent number
US05496956

Reaction notes

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