Acetic Acid → Methyl [2-(5-acetylamino-2-amino-4-fluorophenoxy)phenoxy]acetate

HRID 493938Notes

Reaction equation

HRID 493938 reaction equation
C(O)(=O)C.[C:5]([NH:8][C:9]1[C:10]([F:31])=[CH:11][C:12]([N+:28]([O-])=O)=[C:13]([CH:27]=1)[O:14][C:15]1[CH:26]=[CH:25][CH:24]=[CH:23][C:16]=1[O:17][CH2:18][C:19]([O:21][CH3:22])=[O:20])(=[O:7])[CH3:6]>[Fe].O>[C:5]([NH:8][C:9]1[C:10]([F:31])=[CH:11][C:12]([NH2:28])=[C:13]([CH:27]=1)[O:14][C:15]1[CH:26]=[CH:25][CH:24]=[CH:23][C:16]=1[O:17][CH2:18][C:19]([O:21][CH3:22])=[O:20])(=[O:7])[CH3:6]

Participants

5

Reactant 2

HCID 176Acetic AcidHCID 21053883Methyl [2-(5-acetylamino-4-fluoro-2-nitrophenoxy)phenoxy]acetate

Product 1

HCID 21053882Methyl [2-(5-acetylamino-2-amino-4-fluorophenoxy)phenoxy]acetateYield 72.8%

Reagents, catalysts & solvents 2

HCID 23925IronCatalystHCID 962WaterSolvent2×

Conditions

Temperature
80 °C

Procedure

To a mixture of 40 ml of acetic acid and 40 ml of water was added 2.2 g of iron powder, and the temperature was increased to 80° C. To the mixture was added 3.0 g of methyl [2-(5-acetylamino-4-fluoro-2-nitrophenoxy)phenoxy]acetate, and the mixture was heated at reflux for 30 minutes. The mixture was then poured into water, and the mixture was extracted with ethyl acetate. The organic layer was washed with water and saturated aqueous sodium bicarbonate solution, dried over magnesium sulfate, and then concentrated to give 2.01 g of methyl [2-(5-acetylamino-2-amino-4-fluorophenoxy)phenoxy]acetate.

Workup

  1. temperaturethe mixture was heated
  2. temperatureat reflux for 30 minutes
  3. extractionthe mixture was extracted with ethyl acetate
  4. washThe organic layer was washed with water and saturated aqueous sodium bicarbonate solution
  5. dry with materialdried over magnesium sulfate
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-2f165c7fbc2f49b791de0cc8cf316471
Source dataset
uspto-grants-2009_05
Patent number
US07538072B2

Reaction notes

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