Methyl 3-(difluoromethoxy)-4-nitrobenzoate → Methyl 4-amino-3-(difluoromethoxy)benzoate

HRID 2406299Notes

Reaction equation

HRID 2406299 reaction equation
[F:1][CH:2]([F:17])[O:3][C:4]1[CH:5]=[C:6]([CH:11]=[CH:12][C:13]=1[N+:14]([O-])=O)[C:7]([O:9][CH3:10])=[O:8].[H][H]>C(O)C.[Pd]>[NH2:14][C:13]1[CH:12]=[CH:11][C:6]([C:7]([O:9][CH3:10])=[O:8])=[CH:5][C:4]=1[O:3][CH:2]([F:1])[F:17]

Participants

5

Reactant 2

HCID 57969921Methyl 3-(difluoromethoxy)-4-nitrobenzoateHCID 178418361HCID 178418361, compound

Product 1

HCID 43380209Methyl 4-amino-3-(difluoromethoxy)benzoateYield 75.9%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

Methyl 3-(difluoromethoxy)-4-nitrobenzoate (0.9 g) was placed in a 250 mL round bottom flask and dissolved in 30 mL of ethanol. Pd/C (0.15 g, 10% Pd) was carefully added and a balloon of hydrogen was attached to the flask. The reaction was vigorously stirred over night. After checking by TLC, the reaction was filtered through a pad of celite and concentrated to give 0.6 g of methyl 4-amino-3-(difluoromethoxy)benzoate which was used without further purification.

Workup

  1. filtrationthe reaction was filtered through a pad of celite
  2. concentrationconcentrated

Sources & evidence

ORD record
ord-3429145f23474d48a710de364d2c7dd6
Source dataset
uspto-grants-2014_08
Patent number
US08809331B2

Reaction notes

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