Acetic Acid → 3-(3-Amino-4-chlorophenyl)-1-methyl-4,5-di(trifluoromethyl)-1H-pyrazole

HRID 1005279Notes

Reaction equation

HRID 1005279 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[C:12]([C:13]([F:16])([F:15])[F:14])=[C:11]([C:17]([F:20])([F:19])[F:18])[N:10]([CH3:21])[N:9]=2)=[CH:4][C:3]=1[N+:22]([O-])=O.C(O)(=O)C.O.C(OCC)(=O)C>CO.[Fe]>[NH2:22][C:3]1[CH:4]=[C:5]([C:8]2[C:12]([C:13]([F:14])([F:15])[F:16])=[C:11]([C:17]([F:20])([F:19])[F:18])[N:10]([CH3:21])[N:9]=2)[CH:6]=[CH:7][C:2]=1[Cl:1]

Participants

7

Reactant 4

HCID 176Acetic AcidHCID 962WaterHCID 8857Ethyl AcetateHCID 187910223-(4-Chloro-3-nitrophenyl)-1-methyl-4,5-di(trifluoromethyl)-1H-pyrazole

Product 1

HCID 187910193-(3-Amino-4-chlorophenyl)-1-methyl-4,5-di(trifluoromethyl)-1H-pyrazole

Reagents, catalysts & solvents 2

HCID 23925IronCatalystHCID 887MethanolSolvent

Procedure

A solution of 10 g (26 mmol) of 3-(4-chloro-3-nitrophenyl)-1-methyl-4,5-di(trifluoromethyl)-1H-pyrazole in 50 ml of methanol was added dropwise to a mixture, heated at reflux temperature, of 4.5 g (80 mmol) of iron powder and 30 ml of glacial acetic acid. After the mixture had been stirred for 3 hours it was poured into 100 ml of water. Then, 100 ml of ethyl acetate were added to the mixture. The solids were subsequently separated off from the mixture and washed with ethyl acetate. The organic phase was separated off from the combined filtrates, washed with water, dried over magnesium sulfate and finally concentrated.

Workup

  1. temperatureheated
  2. temperatureat reflux temperature
  3. customThe solids were subsequently separated off from the mixture
  4. washwashed with ethyl acetate
  5. customThe organic phase was separated off from the combined filtrates
  6. washwashed with water
  7. dry with materialdried over magnesium sulfate
  8. concentrationfinally concentrated

Sources & evidence

ORD record
ord-9103c41c4d9d4bf3a5b46987959385f9
Source dataset
uspto-grants-2000_04
Patent number
US06054412

Reaction notes

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