Ethyl 2-fluoro-5-nitrobenzoate → Ethyl 5-amino-2-fluorobenzoate

HRID 1836816Notes

Reaction equation

HRID 1836816 reaction equation
[F:1][C:2]1[CH:12]=[CH:11][C:10]([N+:13]([O-])=O)=[CH:9][C:3]=1[C:4]([O:6][CH2:7][CH3:8])=[O:5]>C(O)C.[Pd]>[NH2:13][C:10]1[CH:11]=[CH:12][C:2]([F:1])=[C:3]([CH:9]=1)[C:4]([O:6][CH2:7][CH3:8])=[O:5]

Participants

4

Reactant 1

HCID 12793176Ethyl 2-fluoro-5-nitrobenzoate

Product 1

HCID 22180191Ethyl 5-amino-2-fluorobenzoateYield 101.6%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

Ethyl 2-fluoro-5-nitrobenzoate (0.63 g) was dissolved in ethanol (10 ml), and 10% Pd—C (0.064 g) was added to the solution. The mixture was subjected to catalytic reduction at room temperature for 7 hr. The reaction solution was filtered through Celite, and was washed with ethanol. The solvent was then removed by distillation under the reduced pressure to give 0.55 g (100%) of ethyl 5-amino-2-fluorobenzoate.

Workup

  1. filtrationThe reaction solution was filtered through Celite
  2. washwas washed with ethanol
  3. customThe solvent was then removed by distillation under the reduced pressure

Sources & evidence

ORD record
ord-951888f75c024911a9f9e0c7319653c0
Source dataset
uspto-grants-2004_08
Patent number
US06777414B1

Reaction notes

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