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

HRID 1244843Notes

Reaction equation

HRID 1244843 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-1653a6ed7cd14d0a8cfd295030b3cc65
Source dataset
uspto-grants-2006_10
Patent number
US07122680B2

Reaction notes

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