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

HRID 2068734Notes

Reaction equation

HRID 2068734 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 9e (58 mg, 0.22 mmol) was dissolved in 1 mL of methanol under stirring at room temperature, and 1 mL of water and sodium hydroxide (15 mg, 0.375 mmol) were then added to the solution. Upon completion of the addition, the reaction mixture was stirred for another 1 hour. The reaction was completed until TLC showed the disappearance of starting materials. The above mixture was filtered, the filter cake was washed with water thrice and dried to give the title compound N-(5-fluoro-2-oxo-2,3-dihydro-1H-indol-6-yl)-2-hydroxy-acetamide 9f (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 above mixture was filtered
  4. washthe filter cake was washed with water thrice
  5. customdried

Sources & evidence

ORD record
ord-2948f422010141b5b743e5487d5a28cc
Source dataset
uspto-grants-2012_10
Patent number
US08299069B2

Reaction notes

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