2-Fluoro-5-methoxy-4-nitrobenzoic acid → 4-Amino-2-fluoro-5-methoxybenzoic acid

HRID 2234453Notes

Reaction equation

HRID 2234453 reaction equation
[F:1][C:2]1[CH:10]=[C:9]([N+:11]([O-])=O)[C:8]([O:14][CH3:15])=[CH:7][C:3]=1[C:4]([OH:6])=[O:5]>C(O)C.[Pd]>[NH2:11][C:9]1[C:8]([O:14][CH3:15])=[CH:7][C:3]([C:4]([OH:6])=[O:5])=[C:2]([F:1])[CH:10]=1

Participants

4

Reactant 1

HCID 579556142-Fluoro-5-methoxy-4-nitrobenzoic acid2×

Product 1

HCID 529829634-Amino-2-fluoro-5-methoxybenzoic acidYield 46%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

2-fluoro-5-methoxy-4-nitrobenzoic acid (Intermediate 12; 7.76 g, 36.1 mmol) was stirred and dissolved in ethanol (200 mL) over 5% Pd/C (770 mg) and hydrogenated at ambient temperature for 4 hours. During this time product precipitated in the reaction. DMF (20 mL) was added to give a solution. The catalyst was filtered off and washed with EtOH and the solvent evaporated. The residue was triturated with diethyl ether to yield the title compound as a dark brown solid (3.06 g, 46%)

Workup

  1. customDuring this time product precipitated in the reaction
  2. additionDMF (20 mL) was added
  3. customto give a solution
  4. filtrationThe catalyst was filtered off
  5. washwashed with EtOH
  6. customthe solvent evaporated
  7. customThe residue was triturated with diethyl ether

Sources & evidence

ORD record
ord-8ae1d301804444018abb21a9bd06b3f3
Source dataset
uspto-grants-2010_05
Patent number
US07709471B2

Reaction notes

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