3-Methoxy-4-nitrobenzoic acid → Methyl 4-amino-3-fluorobenzoate

HRID 1760842Notes

Reaction equation

HRID 1760842 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].COC1C=C(C=CC=1[N+]([O-])=O)C(O)=O>[Pd].C(OCC)(=O)C>[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 787643-Methoxy-4-nitrobenzoic acidHCID 592761Methyl 3-fluoro-4-nitrobenzoate

Product 1

HCID 11182865Methyl 4-amino-3-fluorobenzoate

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8857Ethyl AcetateSolvent

Procedure

150 mg of 10% palladium on charcoal was added to a solution of the above mixture consisting of methyl 3-fluoro-4-nitrobenzoate and 3-methoxy-4-nitrobenzoic acid (1.7 g) in 50 mL ethyl acetate and maintained under H2 (45 psi) for two hours. The reaction mixture was filtered over Celite and concentrated in vacuo. The product was purified by flash chromatography (SiO2, 10% methanol/dichloromethane), giving 0.7 g of methyl 4-amino-3-fluorobenzoate as an off-white solid.

Workup

  1. temperaturemaintained under H2 (45 psi) for two hours
  2. filtrationThe reaction mixture was filtered over Celite
  3. concentrationconcentrated in vacuo
  4. customThe product was purified by flash chromatography (SiO2, 10% methanol/dichloromethane)

Sources & evidence

ORD record
ord-592fd21a0f904438bf2a92f4a40595e4
Source dataset
uspto-grants-2005_01
Patent number
US06844466B2

Reaction notes

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