3,5-difluoro-2-nitrobenzoic acid → 2-Amino-3,5-difluorobenzoic acid

HRID 1041705Notes

Reaction equation

HRID 1041705 reaction equation
[F:1][C:2]1[C:3]([N+:12]([O-])=O)=[C:4]([CH:8]=[C:9]([F:11])[CH:10]=1)[C:5]([OH:7])=[O:6]>[Pd].CO>[NH2:12][C:3]1[C:2]([F:1])=[CH:10][C:9]([F:11])=[CH:8][C:4]=1[C:5]([OH:7])=[O:6]

Participants

4

Reactant 1

HCID 27833653,5-difluoro-2-nitrobenzoic acid

Product 1

HCID 146519732-Amino-3,5-difluorobenzoic acid

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

3,5-Difluoro-2-nitro-benzoic acid (2.908 g, 0.01432 mol), 10% Palladium on Carbon (50% Wet) (0.61 g). and Methanol (15 mL) was shaken under an atmosphere of Hydrogen at 38 PSI overnight. The reaction mixture was filtered through celite and concentrated under reduced pressure and azeotroped with toluene to give 2-Amino-3,5-difluoro-benzoic acid as off white solids (2.44 g, 99%). 1H-NMR (CDCl3): 7.45 (d, 1H, J=9.3 Hz), 7.03 (m, 1H), 5.65 (br s, 2H).

Workup

  1. filtrationThe reaction mixture was filtered through celite and
  2. concentrationconcentrated under reduced pressure
  3. customazeotroped with toluene

Sources & evidence

ORD record
ord-9c33e11c1c774e119fd10bbf06bdd693
Source dataset
uspto-grants-2013_10
Patent number
US08552186B2

Reaction notes

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