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

HRID 433720
Notes
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Reaction equation

HRID 433720 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]
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

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-c5efac5d25854ecab2dc9b578dd1924b
Source dataset
uspto-grants-2003_12
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US06667413B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes