Water → N-(5-Fluoro-2-oxo-2,3-dihydro-1H-indol-6-yl)-2-hydroxyacetamide

HRID 2191448Notes

Reaction equation

HRID 2191448 reaction equation
[F:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][C:10]=1[NH:11][C:12]([CH2:14][O:15]C(=O)C)=[O:13])[NH:7][C:6](=[O:19])[CH2:5]2.O.[OH-].[Na+]>CO>[F:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][C:10]=1[NH:11][C:12](=[O:13])[CH2:14][OH:15])[NH:7][C:6](=[O:19])[CH2:5]2

Participants

5

Reactant 3

HCID 962WaterHCID 14798Sodium HydroxideHCID 59250091acetic acid (5-fluoro-2-oxo-2,3-dihydro-1H-indol-6-ylcarbamoyl)-methyl ester

Product 1

HCID 45118149N-(5-Fluoro-2-oxo-2,3-dihydro-1H-indol-6-yl)-2-hydroxyacetamideYield 93.8%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Acetic acid (5-fluoro-2-oxo-2,3-dihydro-1H-indol-6-ylcarbamoyl)-methyl ester 27a (58 mg, 0.22 mmol) was dissolved in 1 ml of methanol under stirring, and added with 1 ml of water and sodium hydroxide (15 mg, 0.375 mmol) to the solution at room temperature. Upon completion of the addition, the reaction mixture was stirred for another 1 hour. After thin lay chromatography showed the disappearance of starting materials, the reaction mixture was filtered. The resulting solid was washed with water for three times and dried to obtain the title compound N-(5-fluoro-2-oxo-2,3-dihydro-1H-indol-6-yl)-2-hydroxy-acetamide 27b (46 mg, yield 93.8%) as a gray solid.

Workup

  1. additionUpon completion of the addition
  2. stirringthe reaction mixture was stirred for another 1 hour
  3. filtrationthe reaction mixture was filtered
  4. washThe resulting solid was washed with water for three times
  5. customdried

Sources & evidence

ORD record
ord-b3654e81d97646e9a414a573722fca09
Source dataset
uspto-grants-2012_12
Patent number
US08329682B2

Reaction notes

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