Ethanol → Methyl 4-amino-3-fluorobenzoate

HRID 1452950Notes

Reaction equation

HRID 1452950 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].CCO>[Pd].CCOC(C)=O>[NH2:12][C:11]1[CH:10]=[CH:9][C:4]([C:5]([O:7][CH3:8])=[O:6])=[CH:3][C:2]=1[F:1]

Participants

5

Reactant 2

HCID 702EthanolHCID 592761Methyl 3-fluoro-4-nitrobenzoate

Product 1

HCID 11182865Methyl 4-amino-3-fluorobenzoateYield 95%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8857Ethyl AcetateSolvent

Procedure

Methyl 3-fluoro-4-nitrobenzoate (5.18 g, 26.0 mmol) in a 1:1 mixture (50 mL) of EtOH and AcOEt with 10% Pd/C (0.52 g) was hydrogenated on a Parr hydrogenation apparatus at 40 psi. Pd/C was removed by filtration through a pad of Celite® 545. The filtrate was concentrated under vacuum. The residue was diluted with AcOEt, washed with brine, and dried over anhydrous MgSO4. Evaporation of solvent under vacuum gave the title compound (4.17 g, 95% yield) as a pale solid.

Workup

  1. customPd/C was removed by filtration through a pad of Celite® 545
  2. concentrationThe filtrate was concentrated under vacuum
  3. additionThe residue was diluted with AcOEt
  4. washwashed with brine
  5. dry with materialdried over anhydrous MgSO4
  6. customEvaporation of solvent under vacuum

Sources & evidence

ORD record
ord-f479187110ab4307b28203e22e899385
Source dataset
uspto-grants-2009_01
Patent number
US07473784B2

Reaction notes

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