Methyl 3-fluoro-4-nitrobenzoate → Methyl 4-amino-3-fluorobenzoate

HRID 55379Notes

Reaction equation

HRID 55379 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([CH:9]=[CH:10][C:11]=1[N+:12]([O-])=O)[C:5]([O:7][CH3:8])=[O:6].[H][H]>C(OCC)(=O)C.[Pd]>[F:1][C:2]1[CH:3]=[C:4]([CH:9]=[CH:10][C:11]=1[NH2:12])[C:5]([O:7][CH3:8])=[O:6]

Participants

5

Reactant 2

HCID 592761Methyl 3-fluoro-4-nitrobenzoateHCID 178418361HCID 178418361, compound

Product 1

HCID 11182865Methyl 4-amino-3-fluorobenzoateYield 99.7%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8857Ethyl AcetateSolvent

Procedure

In 150 ml ethyl acetate was dissolved 5.74 grams methyl 3-fluoro-4-nitrobenzoate and the resulting solution was hydrogenated in the Parr apparatus (45 psi) over 600 mg 10% Pd-on-C for about 45 minutes, when the hydrogen uptake ceased. The catalyst was removed by filtration and the solvent was removed in vacuo to give 4.86 grams methyl 3-fluoro-4-aminobenzoate as an off-white solid, m.p. 107°-110° C.

Workup

  1. customThe catalyst was removed by filtration
  2. customthe solvent was removed in vacuo

Sources & evidence

ORD record
ord-1425f6c613514eafb73670cedd89f5f3
Source dataset
uspto-grants-1997_04
Patent number
US05624957

Reaction notes

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