Water → N-[4-amino-2-fluoro-5-{2-(methoxycarbonyl)methoxy-3-pyridyl oxy}phenyl]acetamide

HRID 1862225Notes

Reaction equation

HRID 1862225 reaction equation
O.[F:2][C:3]1[CH:8]=[C:7]([N+:9]([O-])=O)[C:6]([O:12][C:13]2[C:14]([O:19][CH2:20][C:21]([O:23][CH3:24])=[O:22])=[N:15][CH:16]=[CH:17][CH:18]=2)=[CH:5][C:4]=1[NH:25][C:26](=[O:28])[CH3:27]>C(O)(=O)C.C(OCC)(=O)C.[Fe]>[NH2:9][C:7]1[C:6]([O:12][C:13]2[C:14]([O:19][CH2:20][C:21]([O:23][CH3:24])=[O:22])=[N:15][CH:16]=[CH:17][CH:18]=2)=[CH:5][C:4]([NH:25][C:26](=[O:28])[CH3:27])=[C:3]([F:2])[CH:8]=1

Participants

6

Reactant 2

HCID 962WaterHCID 21933549N-[2-fluoro-5-{2-(methoxycarbonyl)methoxy-3-pyridyloxy}-4-nitrophenyl]acetamide

Product 1

HCID 21933527N-[4-amino-2-fluoro-5-{2-(methoxycarbonyl)methoxy-3-pyridyl oxy}phenyl]acetamideYield 91.4%

Reagents, catalysts & solvents 3

HCID 23925IronCatalystHCID 176Acetic AcidSolvent2×HCID 8857Ethyl AcetateSolvent

Conditions

Temperature
45 °C

Procedure

To a mixture of 3.6 g of an iron powder, 10 ml of acetic acid and 1 ml of water was added a solution of 3.67 g of N-[2-fluoro-5-{2-(methoxycarbonyl)methoxy-3-pyridyloxy}-4-nitrophenyl]acetamide in 12 ml of acetic acid and 2 ml of ethyl acetate, dropwise while maintaining the temperature of the reaction solution at 45° C. or lower. After completion of the addition, the mixture was stirred for 1 hour at 40° C., then, the reaction mixture was filtrated through Celite, and concentrated. The residue was diluted with saturated aqueous sodium bicarbonate solution, and extracted with ethyl acetate. The organic layer was washed with saturated aqueous sodium bicarbonate solution, dried over anhydrous magnesium sulfate, and concentrated. Then, the resulted residue was washed with diisopropyl ether to obtain 3.09 g of N-[4-amino-2-fluoro-5-{2-(methoxycarbonyl)methoxy-3-pyridyl oxy}phenyl]acetamide.

Workup

  1. additionAfter completion of the addition
  2. filtrationthe reaction mixture was filtrated through Celite
  3. concentrationconcentrated
  4. additionThe residue was diluted with saturated aqueous sodium bicarbonate solution
  5. extractionextracted with ethyl acetate
  6. washThe organic layer was washed with saturated aqueous sodium bicarbonate solution
  7. dry with materialdried over anhydrous magnesium sulfate
  8. concentrationconcentrated
  9. washThen, the resulted residue was washed with diisopropyl ether

Sources & evidence

ORD record
ord-8a09c8dffc424929a10809ed4221c01f
Source dataset
uspto-grants-2003_03
Patent number
US06537948B1

Reaction notes

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