Acetic Acid → HCID 66990429, compound

HRID 454529Notes

Reaction equation

HRID 454529 reaction equation
O.C([O-])=O.[Na+].C(O)(=O)C.[F:10][CH:11]([F:35])[O:12][C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=1[C:19]1[CH:31]=[CH:30][C:22]([C:23]([O:25][C:26]([CH3:29])([CH3:28])[CH3:27])=[O:24])=[C:21]([N+:32]([O-])=O)[CH:20]=1>[C].[Pd].CC(O)C>[NH2:32][C:21]1[CH:20]=[C:19]([C:14]2[CH:15]=[CH:16][CH:17]=[CH:18][C:13]=2[O:12][CH:11]([F:10])[F:35])[CH:31]=[CH:30][C:22]=1[C:23]([O:25][C:26]([CH3:29])([CH3:28])[CH3:27])=[O:24]

Participants

7

Reactant 4

HCID 176Acetic AcidHCID 962WaterHCID 2723810Sodium FormateHCID 66990208HCID 66990208, compound

Product 1

HCID 66990429HCID 66990429, compoundYield 90.8%

Reagents, catalysts & solvents 2

HCID 178418390HCID 178418390, compoundCatalystHCID 3776IsopropanolSolvent

Procedure

Water (0.53 mL), sodium formate (0.13 g), acetic acid (0.13 mL), and 10% palladium-carbon (35 mg) were added to a 2-propanol (2.1 mL) solution of tert-butyl 4-(2-(difluoromethoxy)phenyl)-2-nitrobenzoate (0.18 g), followed by heating to reflux for 2 hours. The reaction mixture was cooled to room temperature, and then the insoluble substance was removed by filtration. The solvent was evaporated under reduced pressure, and ethyl acetate and a saturated aqueous solution of sodium bicarbonate were added thereto. The organic layer was separated, washed with a saturated aqueous solution of sodium chloride, and dried over anhydrous magnesium sulfate, and the solvent was evaporated under reduced pressure. The obtained residue was purified by silica gel column chromatography [eluent: 99-91% hexane/ethyl acetate] to obtain 0.15 g of tert-butyl 2-amino-4-(2-(difluoromethoxy)phenyl)benzoate as a yellow oily substance.

Workup

  1. temperatureby heating
  2. temperatureto reflux for 2 hours
  3. customthe insoluble substance was removed by filtration
  4. customThe solvent was evaporated under reduced pressure, and ethyl acetate
  5. additiona saturated aqueous solution of sodium bicarbonate were added
  6. customThe organic layer was separated
  7. washwashed with a saturated aqueous solution of sodium chloride
  8. dry with materialdried over anhydrous magnesium sulfate
  9. customthe solvent was evaporated under reduced pressure
  10. customThe obtained residue was purified by silica gel column chromatography [eluent: 99-91% hexane/ethyl acetate]

Sources & evidence

ORD record
ord-04bce31e823f4a2f9746efc36568695e
Source dataset
uspto-grants-2013_07
Patent number
US08492582B2

Reaction notes

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