3-Fluoro-5-nitrobenzoic acid → 3-Amino-5-fluorobenzoic acid

HRID 250718Notes

Reaction equation

HRID 250718 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([CH:8]=[C:9]([N+:11]([O-])=O)[CH:10]=1)[C:5]([OH:7])=[O:6]>[OH-].[OH-].[Pd+2].CO>[F:1][C:2]1[CH:3]=[C:4]([CH:8]=[C:9]([NH2:11])[CH:10]=1)[C:5]([OH:7])=[O:6]

Participants

4

Reactant 1

HCID 27590473-Fluoro-5-nitrobenzoic acid

Product 1

HCID 179151483-Amino-5-fluorobenzoic acid

Reagents, catalysts & solvents 2

HCID 9942167Palladium hydroxideCatalystHCID 887MethanolSolvent

Procedure

Into a Parr pressure reactor were added 3-fluoro-5-nitrobenzoic acid (667, 5.0 g, 0.027 mol), methanol (50.0 mL), 20% Pd(OH)2 on carbon (300 mg). The reaction was shaken under an atmosphere of hydrogen at 50 psi overnight. The reaction was filtered through celite and was concentrated to dryness to provide a white solid (668, 4.0 g, 95.0%).

Workup

  1. filtrationThe reaction was filtered through celite
  2. concentrationwas concentrated to dryness
  3. customto provide a white solid (668, 4.0 g, 95.0%)

Sources & evidence

ORD record
ord-c6a370535f03424f80c1d391ad1932b9
Source dataset
uspto-grants-2011_01
Patent number
US07863288B2

Reaction notes

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