Acetyl chloride → 5-acetyl-2,3-dihydro-1H-indol-2-one

HRID 347942Notes

Reaction equation

HRID 347942 reaction equation
[Cl-].[Al+3].[Cl-].[Cl-].[C:5](Cl)(=[O:7])[CH3:6].[NH:9]1[C:17]2[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=2)[CH2:11][C:10]1=[O:18]>ClCCCl.O>[C:5]([C:14]1[CH:13]=[C:12]2[C:17](=[CH:16][CH:15]=1)[NH:9][C:10](=[O:18])[CH2:11]2)(=[O:7])[CH3:6]

Participants

6

Reactant 3

HCID 6367Acetyl chlorideHCID 321710OxindoleHCID 6451240Aluminum(III) Chloride

Product 1

HCID 102196435-acetyl-2,3-dihydro-1H-indol-2-one

Reagents, catalysts & solvents 2

HCID 111,2-DichloroethaneSolventHCID 962WaterSolvent

Procedure

171 g (1.28 mol) aluminium chloride in 500 ml 1,2-dichloroethane are cooled in the ice bath. Then 78 g (1.1 mol) acetylchloride are added dropwise, so that the temperature does not exceed 10° C. After 1 h, 71.3 g (0.53 mol) 2-indolinone (1,3-dihydro-indol-2-one) are added in 4 batches and the temperature is kept at 10–12° C. The reaction mixture is left overnight to warm up slowly to ambient temperature. Then the solution is slowly added to 1 kg ice with vigorous stirring. The slurry is diluted with 1 l water and stirred for another 30 min. Then the precipitate is suction filtered.

Workup

  1. customdoes not exceed 10° C
  2. customis kept at 10–12° C
  3. waitThe reaction mixture is left overnight
  4. filtrationfiltered

Sources & evidence

ORD record
ord-af3f156270b84887b1f308ec9206550e
Source dataset
uspto-grants-2007_02
Patent number
US07176231B2

Reaction notes

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