N-[4-chloro-2-fluoro-5-{2-(methoxycarbonyl)methoxy-3-pyridyloxy}phenyl]acetamide → 4-Chloro-2-fluoro-5-{2-(methoxycarbonyl)methoxy-3-pyridyloxy}aniline

HRID 493947Notes

Reaction equation

HRID 493947 reaction equation
[Cl:1][C:2]1[C:7]([O:8][C:9]2[C:10]([O:15][CH2:16][C:17]([O:19][CH3:20])=[O:18])=[N:11][CH:12]=[CH:13][CH:14]=2)=[CH:6][C:5]([NH:21]C(=O)C)=[C:4]([F:25])[CH:3]=1>CO>[Cl:1][C:2]1[C:7]([O:8][C:9]2[C:10]([O:15][CH2:16][C:17]([O:19][CH3:20])=[O:18])=[N:11][CH:12]=[CH:13][CH:14]=2)=[CH:6][C:5]([NH2:21])=[C:4]([F:25])[CH:3]=1

Participants

3

Reactant 1

HCID 21933517N-[4-chloro-2-fluoro-5-{2-(methoxycarbonyl)methoxy-3-pyridyloxy}phenyl]acetamide

Product 1

HCID 219335774-Chloro-2-fluoro-5-{2-(methoxycarbonyl)methoxy-3-pyridyloxy}anilineYield 94.4%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

First, 20 ml of a methanol solution of a boron trifluoride methanol complex was mixed with 1.04 g of N-[4-chloro-2-fluoro-5-{2-(methoxycarbonyl)methoxy-3-pyridyloxy}phenyl]acetamide, and the mixture was stirred at 60° C. to 70° C. for 3 hours and then concentrated. The residue was diluted with saturated aqueous sodium bicarbonate solution, and the mixture was extracted with ethyl acetate. The organic layer was washed with saturated aqueous sodium chloride solution, dried over anhydrous magnesium sulfate, and then concentrated. The residue was subjected to column chromatography to give 0.87 g of 4-chloro-2-fluoro-5-{2-(methoxycarbonyl)methoxy-3-pyridyloxy}aniline.

Workup

  1. concentrationconcentrated
  2. additionThe residue was diluted with saturated aqueous sodium bicarbonate solution
  3. extractionthe mixture was extracted with ethyl acetate
  4. washThe organic layer was washed with saturated aqueous sodium chloride solution
  5. dry with materialdried over anhydrous magnesium sulfate
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-b57c66b6e5914fa8bd5166662a186f5f
Source dataset
uspto-grants-2009_05
Patent number
US07538072B2

Reaction notes

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