Hydrochloric Acid → N-(5-fluoro-2-oxo-2,3-dihydro-1H-indol-6-yl)-2-hydroxy-propionamide

HRID 2191416Notes

Reaction equation

HRID 2191416 reaction equation
[F:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][C:10]=1[NH:11][C:12]([CH:14]([O:16]C(=O)C)[CH3:15])=[O:13])[NH:7][C:6](=[O:20])[CH2:5]2.O.[OH-].[Na+].Cl>CO>[F:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][C:10]=1[NH:11][C:12](=[O:13])[CH:14]([OH:16])[CH3:15])[NH:7][C:6](=[O:20])[CH2:5]2

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 962WaterHCID 14798Sodium HydroxideHCID 59250052acetic acid 1-(5-fluoro-2-oxo-2,3-dihydro-1H-indol-6-ylcarbamoyl)-ethyl ester

Product 1

HCID 66607967N-(5-fluoro-2-oxo-2,3-dihydro-1H-indol-6-yl)-2-hydroxy-propionamideYield 70%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Acetic acid 1-(5-fluoro-2-oxo-2,3-dihydro-1H-indol-6-ylcarbamoyl)-ethyl ester 8a (1.86 g, 6.4 mmol) was dissolved in 20 ml of methanol under stirring, and added with 10 ml of water and sodium hydroxide solution (10 ml, 0.7 mol/L) to the solution and stirred for 4 hours at room temperature. After thin lay chromatography showed the disappearance of starting materials, the reaction mixture was neutralized with hydrochloride acid (1 mol/L) and concentrated under reduced pressure. The residue was purified by silica gel column chromatography and dried to obtain N-(5-fluoro-2-oxo-2,3-dihydro-1H-indol-6-yl)-2-hydroxy-propionamide 8b (1.0 g, yield 70%) as a white solid.

Workup

  1. stirringstirred for 4 hours at room temperature
  2. concentrationconcentrated under reduced pressure
  3. customThe residue was purified by silica gel column chromatography
  4. customdried

Sources & evidence

ORD record
ord-a3fa4cb35176491a8c469983bad2a690
Source dataset
uspto-grants-2012_12
Patent number
US08329682B2

Reaction notes

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