Acetic Anhydride → 1-Acetyl-4-(acetyloxy)-1,3-dihydro-2H-indol-2-one

HRID 2416938Notes

Reaction equation

HRID 2416938 reaction equation
[C:1]([O:4][C:5]1[CH:13]=[CH:12][CH:11]=[C:10]2[C:6]=1[CH2:7][C:8](=[O:14])[NH:9]2)(=[O:3])[CH3:2].C(=O)([O-])[O-].[Na+].[Na+].[C:21](OC(=O)C)(=[O:23])[CH3:22]>O1CCCC1>[C:21]([N:9]1[C:10]2[C:6](=[C:5]([O:4][C:1](=[O:3])[CH3:2])[CH:13]=[CH:12][CH:11]=2)[CH2:7][C:8]1=[O:14])(=[O:23])[CH3:22]

Participants

5

Reactant 3

HCID 7918Acetic AnhydrideHCID 10340Sodium CarbonateHCID 10465147HCID 10465147, compound

Product 1

HCID 202278901-Acetyl-4-(acetyloxy)-1,3-dihydro-2H-indol-2-oneYield 27.4%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a mixture of 4-(acetyloxy)-1,3-dihydro-2H-indol-2-one (J. Med. Chem., 38:2802-2808, 1995; 1.44 g, 7.5 mmol) and sodium carbonate (5.3 g, 50 mmol) in tetrahydrofuran (50 mL) is added acetic anhydride (4.3 mL, 45 mmol). The mixture is stirred at ambient temperature for 18 hours, and partitioned between ethyl acetate and water. After drying (magnesium sulfate), the solvent is removed in vacuo. The crude material is preadsorbed on silica gel (10 g), and purified by flash chromtography (90 g SiO2, 10% ethyl acetate:hexane to 70% ethyl acetate:hexane, linear gradient over 30 minutes) to provide 480 mg (27%) of acetic acid 1-acetyl-2-oxo-2,3-dihydro-1H-indol-4-yl ester as a white solid.

Workup

  1. custompartitioned between ethyl acetate and water
  2. dry with materialAfter drying (magnesium sulfate)
  3. customthe solvent is removed in vacuo
  4. custompurified by flash chromtography (90 g SiO2, 10% ethyl acetate:hexane to 70% ethyl acetate:hexane, linear gradient over 30 minutes)

Sources & evidence

ORD record
ord-88581aaade9a4e26a9db3417ac81c5ae
Source dataset
uspto-grants-2004_11
Patent number
US06825220B2

Reaction notes

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