Acetic Acid → HCID 58508431, compound

HRID 454494Notes

Reaction equation

HRID 454494 reaction equation
C([O-])=O.[Na+].[CH3:5][O:6][C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][C:8]=1[C:13]1[CH:25]=[CH:24][C:16]([C:17]([O:19][C:20]([CH3:23])([CH3:22])[CH3:21])=[O:18])=[C:15]([N+:26]([O-])=O)[CH:14]=1.C(O)(=O)C>CC(O)C.O.[C].[Pd]>[NH2:26][C:15]1[CH:14]=[C:13]([C:8]2[CH:9]=[CH:10][CH:11]=[CH:12][C:7]=2[O:6][CH3:5])[CH:25]=[CH:24][C:16]=1[C:17]([O:19][C:20]([CH3:22])([CH3:23])[CH3:21])=[O:18]

Participants

7

Reactant 3

HCID 176Acetic AcidHCID 2723810Sodium FormateHCID 58508546HCID 58508546, compound

Product 1

HCID 58508431HCID 58508431, compoundYield 100%

Reagents, catalysts & solvents 3

HCID 178418390HCID 178418390, compoundCatalystHCID 962WaterSolventHCID 3776IsopropanolSolvent

Procedure

Sodium formate (2.7 g) and 10% palladium-carbon (0.65 g) were sequentially added to a solution mixture of tert-butyl 4-(2-methoxyphenyl)-2-nitrobenzoate (3.3 g) in 2-propanol (40 mL), water (10 mL), and acetic acid (2.6 mL), 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 a saturated aqueous solution of sodium bicarbonate and ethyl acetate were added to the residue. 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 3.0 g of tert-butyl 2-amino-4-(2-methoxyphenyl)benzoate as a white 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
  5. additiona saturated aqueous solution of sodium bicarbonate and ethyl acetate were added to the residue
  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-ba169f6166a54eb5b2f43be93bae5d89
Source dataset
uspto-grants-2013_07
Patent number
US08492582B2

Reaction notes

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