Methyl 4-fluoro-3-nitrobenzoate → Methyl 3-amino-4-fluorobenzoate

HRID 2244017Notes

Reaction equation

HRID 2244017 reaction equation
[CH3:1][O:2][C:3](=[O:14])[C:4]1[CH:9]=[CH:8][C:7]([F:10])=[C:6]([N+:11]([O-])=O)[CH:5]=1.[H][H]>C(O)C.[Pd]>[CH3:1][O:2][C:3](=[O:14])[C:4]1[CH:9]=[CH:8][C:7]([F:10])=[C:6]([NH2:11])[CH:5]=1

Participants

5

Reactant 2

HCID 5219721Methyl 4-fluoro-3-nitrobenzoateHCID 178418361HCID 178418361, compound

Product 1

HCID 12541234Methyl 3-amino-4-fluorobenzoateYield 89%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

Stir mixture of 4-fluoro-3-nitro-benzoic acid methyl ester (5.30 g, 26.6 mmol) and palladium (5% on carbon, 5.66 g, 2.66 mmol, Aldrich Chemical Co.) in ethanol (0.2 M). Carefully introduce hydrogen (balloon) and stir the reaction for 24 h. Filter the reaction mixture through a glass-fiber filter and wash the filter cake with ethanol. Concentrate the filtrate to afford the title compound (4.00 g, 23.6 mmol, 89%): MS (m/z): 170 (M+1).

Workup

  1. customthe reaction for 24 h
  2. filtrationFilter the reaction mixture through a glass-fiber
  3. filtrationfilter
  4. washwash the filter cake with ethanol
  5. concentrationConcentrate the filtrate

Sources & evidence

ORD record
ord-99f4863e089f4e7da071aa293ef2fdf8
Source dataset
uspto-grants-2010_03
Patent number
US07678794B2

Reaction notes

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