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

HRID 2191475Notes

Reaction equation

HRID 2191475 reaction equation
[O:1]=[C:2]1[CH2:10][C:9]2[C:4](=[CH:5][CH:6]=[C:7]([NH:11][C:12]([CH2:14][O:15]C(=O)C)=[O:13])[CH:8]=2)[NH:3]1.[OH-].[Na+].Cl>CO>[OH:15][CH2:14][C:12]([NH:11][C:7]1[CH:8]=[C:9]2[C:4](=[CH:5][CH:6]=1)[NH:3][C:2](=[O:1])[CH2:10]2)=[O:13]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 59250067acetic acid (2-oxo-2,3-dihydro-1H-indol-5-ylcarbamoyl)-methyl ester

Product 1

HCID 592500772-hydroxy-N-(2-oxo-2,3-dihydro-1H-indol-5-yl)-acetamideYield 19.5%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Acetic acid (2-oxo-2,3-dihydro-1H-indol-5-ylcarbamoyl)-methyl ester 44a (2.43 g, 10 mmol) was dissolved in 60 ml of methanol under stirring, and sodium hydroxide solution (20 ml, 2 mol/L) was added to the solution and stirred at room temperature overnight. After thin lay chromatography showed the disappearance of starting materials, the reaction mixture was neutralized with hydrochloric acid solution (6 mol/L) in ice-water bath, concentrated under reduced pressure. The resulting solid was purified by silica gel column chromatography to obtain the title compound 2-hydroxy-N-(2-oxo-2,3-dihydro-1H-indol-5-yl)-acetamide 44b (402 mg, yield 19.5%) as a yellow solid.

Workup

  1. stirringstirred at room temperature overnight
  2. concentrationconcentrated under reduced pressure
  3. customThe resulting solid was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-3d2a3b80c4b940e780fcc35f1c0624c4
Source dataset
uspto-grants-2012_12
Patent number
US08329682B2

Reaction notes

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