Ethyl Acetate → Methyl 4-amino-3-(trifluoromethyl)benzoate

HRID 1161352Notes

Reaction equation

HRID 1161352 reaction equation
[CH3:1][O:2][C:3](=[O:17])[C:4]1[CH:9]=[CH:8][C:7]([N+:10]([O-])=O)=[C:6]([C:13]([F:16])([F:15])[F:14])[CH:5]=1.C(OCC)(=O)C>CO>[CH3:1][O:2][C:3](=[O:17])[C:4]1[CH:9]=[CH:8][C:7]([NH2:10])=[C:6]([C:13]([F:14])([F:16])[F:15])[CH:5]=1

Participants

4

Reactant 2

HCID 8857Ethyl AcetateHCID 46311177Methyl 4-nitro-3-(trifluoromethyl)benzoate

Product 1

HCID 25067388Methyl 4-amino-3-(trifluoromethyl)benzoateYield 98%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of 4.0 g (16.1 mmol) 4-nitro-3-trifluoromethyl-benzoic acid methyl ester in 50 mL methanol 0.4 g 10% palladium on charcoal was added and the suspension stirred for 2 h at room temperature under an atmosphere of hydrogen (1.7 bar). After the addition of 100 mL ethyl acetate the catalyst was filtered off, the filtrate evaporated and dried under high vacuum to give the title compound as a white solid (98%) which was used in the next step without further purification.

Workup

  1. filtrationwas filtered off
  2. customthe filtrate evaporated
  3. customdried under high vacuum

Sources & evidence

ORD record
ord-ca70608de9d740d0b385792c0a9edcd3
Source dataset
uspto-grants-2010_10
Patent number
US07816540B2

Reaction notes

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