O-Xylene → 1-acetyl-6-bromo-3-methyl-1,3-dihydro-2H-indol-2-one

HRID 1942533Notes

Reaction equation

HRID 1942533 reaction equation
[Br:1][C:2]1[CH:10]=[C:9]2[C:5]([CH:6]([CH3:12])[C:7](=[O:11])[NH:8]2)=[CH:4][CH:3]=1.[C:13](OC(=O)C)(=[O:15])[CH3:14].C1(C)C(C)=CC=CC=1>O>[C:13]([N:8]1[C:9]2[C:5](=[CH:4][CH:3]=[C:2]([Br:1])[CH:10]=2)[CH:6]([CH3:12])[C:7]1=[O:11])(=[O:15])[CH3:14]

Participants

5

Reactant 3

HCID 7237O-XyleneHCID 7918Acetic AnhydrideHCID 2803186-bromo-3-methyl-2,3-dihydro-1H-indol-2-one

Product 1

HCID 108257591-acetyl-6-bromo-3-methyl-1,3-dihydro-2H-indol-2-one

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To 6-bromo-3-methyl-1,3-dihydro-2H-indol-2-one (11.2 g) were added acetic anhydride (12 ml) and xylene (120 ml), and the mixture was refluxed for 5 hours. After the reaction was complete, water was added to the reaction solution, and the mixture was extracted with ethyl acetate solution. This ethyl acetate solution was washed successively with water, a saturated aqueous sodium hydrogen carbonate solution and an aqueous sodium chloride solution, dried over magnesium sulfate, filtered, and concentrated. The obtained residue was purified by silica gel column chromatography (hexane/ethyl acetate=4/1) to give the title compound (9.5 g) as a red solid.

Workup

  1. temperaturethe mixture was refluxed for 5 hours
  2. extractionthe mixture was extracted with ethyl acetate solution
  3. washThis ethyl acetate solution was washed successively with water
  4. dry with materiala saturated aqueous sodium hydrogen carbonate solution and an aqueous sodium chloride solution, dried over magnesium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customThe obtained residue was purified by silica gel column chromatography (hexane/ethyl acetate=4/1)

Sources & evidence

ORD record
ord-c0aab954eea64d7d89a04692eb117165
Source dataset
uspto-grants-2013_03
Patent number
US08389511B2

Reaction notes

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