Methyl 4,5-difluoro-2-nitrobenzoate → Methyl 2-amino-4,5-difluorobenzoate

HRID 1172575Notes

Reaction equation

HRID 1172575 reaction equation
[F:1][C:2]1[C:11]([F:12])=[CH:10][C:5]([C:6]([O:8][CH3:9])=[O:7])=[C:4]([N+:13]([O-])=O)[CH:3]=1>CCOC(C)=O.[Pd]>[NH2:13][C:4]1[CH:3]=[C:2]([F:1])[C:11]([F:12])=[CH:10][C:5]=1[C:6]([O:8][CH3:9])=[O:7]

Participants

4

Reactant 1

HCID 21928432Methyl 4,5-difluoro-2-nitrobenzoate

Product 1

HCID 18472001Methyl 2-amino-4,5-difluorobenzoate

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of methyl 4,5-difluoro-2-nitrobenzoate 1b (23.0 g, 106 mmol) in EtOAc (200 mL), was added 10% Pd/C (wet, 50% water, 6.0 g), and the mixture was shaken on a Parr hydrogenator at 50 PSI for 3 hr. The reaction mixture was then filtered through a celite pad and the filtrate was concentrated by rotary evaporation to yield methyl 2-amino-4,5-difluorobenzoate 1c as a colorless solid, 19.0 g (96%).

Workup

  1. filtrationThe reaction mixture was then filtered through a celite pad
  2. concentrationthe filtrate was concentrated by rotary evaporation

Sources & evidence

ORD record
ord-45385cb6efd6409489cbe974d0784412
Source dataset
uspto-grants-2010_11
Patent number
US07834023B2

Reaction notes

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