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

HRID 1280368Notes

Reaction equation

HRID 1280368 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

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

Workup

  1. temperaturethe mixture was heated for 30 minutes
  2. temperatureunder reflux
  3. extractionextracted with ethyl acetate
  4. washthe organic layer was washed with water
  5. washwashed with saturated aqueous sodium bicarbonate
  6. dry with materialdried over magnesium sulfate
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-ea1ce02c79284a1a906057975cc72a25
Source dataset
uspto-grants-2002_09
Patent number
US06451740B2

Reaction notes

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