Methyl 2-fluoro-4-nitrobenzoate → Methyl 4-amino-2-fluorobenzoate

HRID 1843048Notes

Reaction equation

HRID 1843048 reaction equation
[F:1][C:2]1[CH:11]=[C:10]([N+:12]([O-])=O)[CH:9]=[CH:8][C:3]=1[C:4]([O:6][CH3:7])=[O:5]>CCO.[Pd]>[NH2:12][C:10]1[CH:9]=[CH:8][C:3]([C:4]([O:6][CH3:7])=[O:5])=[C:2]([F:1])[CH:11]=1

Participants

4

Reactant 1

HCID 3013872Methyl 2-fluoro-4-nitrobenzoate

Product 1

HCID 21957875Methyl 4-amino-2-fluorobenzoateYield 96.5%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

To a stirred solution of methyl 2-fluoro-4-nitrobenzoate (1 g, 4.9 mmol, 1.0 eq) in EtOH (15 mL) was added 10% Pd/C (300 mg) and stirred under hydrogen gas balloon pressure. The reaction mixture was passed through celite, washed with EtOAC, the filtrate was concentrated to obtain methyl 4-amino-2-fluorobenzoate (800 mg; 95%) as a pale yellow solid (TLC: EtOAc/PE (2:3); Rf: 0.2).

Workup

  1. washwashed with EtOAC
  2. concentrationthe filtrate was concentrated

Sources & evidence

ORD record
ord-5d0242af1d5741f5b1878e26e88cca3a
Source dataset
uspto-grants-2015_02
Patent number
US08946204B2

Reaction notes

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