4-Nitro-3-trifluoromethyl-phenoxyethyl acetate → 4-Amino-3-trifluoromethyl-phenoxyethyl acetate

HRID 383535Notes

Reaction equation

HRID 383535 reaction equation
[C:1]([O:4][CH2:5][CH2:6][O:7][C:8]1[CH:13]=[CH:12][C:11]([N+:14]([O-])=O)=[C:10]([C:17]([F:20])([F:19])[F:18])[CH:9]=1)(=[O:3])[CH3:2].[H][H]>[C].[Pd].C(OCC)(=O)C>[C:1]([O:4][CH2:5][CH2:6][O:7][C:8]1[CH:13]=[CH:12][C:11]([NH2:14])=[C:10]([C:17]([F:18])([F:19])[F:20])[CH:9]=1)(=[O:3])[CH3:2]

Participants

5

Reactant 2

HCID 675200144-Nitro-3-trifluoromethyl-phenoxyethyl acetateHCID 178418361HCID 178418361, compound

Product 1

HCID 675199904-Amino-3-trifluoromethyl-phenoxyethyl acetateYield 121.1%

Reagents, catalysts & solvents 2

HCID 178418390HCID 178418390, compoundCatalystHCID 8857Ethyl AcetateSolvent

Procedure

In the ethyl acetate (30 mL) solution of 4-nitro-3-trifluoromethyl-phenoxyethyl acetate (3.24 g (theoretical amount: 2.83 g, 9.66 mmol) which had been obtained in 1), 10% palladium carbon (0.3 g) was added and hydrogen was added. After the catalyst had been separated by filtration, the solvent was removed by distillation under reduced pressure and crude 4-amino-3-trifluoromethyl-phenoxyethyl acetate (BB03, 3.08 g (theoretical amount: 2.54 g) 100%) was obtained as oily matter.

Workup

  1. customAfter the catalyst had been separated by filtration
  2. customthe solvent was removed by distillation under reduced pressure

Sources & evidence

ORD record
ord-3c05c094cea14c74a26725818ae569bc
Source dataset
uspto-grants-2013_02
Patent number
US08367666B2

Reaction notes

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