Butyryl chloride → 5-Butyryl-2-indolinone

HRID 366594Notes

Reaction equation

HRID 366594 reaction equation
[Cl-].[Al+3].[Cl-].[Cl-].[NH:5]1[C:13]2[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=2)[CH2:7][C:6]1=[O:14].[C:15](Cl)(=[O:19])[CH2:16][CH2:17][CH3:18]>ClCCCl>[C:15]([C:10]1[CH:9]=[C:8]2[C:13](=[CH:12][CH:11]=1)[NH:5][C:6](=[O:14])[CH2:7]2)(=[O:19])[CH2:16][CH2:17][CH3:18]

Participants

5

Reactant 3

HCID 8855Butyryl chlorideHCID 321710OxindoleHCID 6451240Aluminum(III) Chloride

Product 1

HCID 235593785-Butyryl-2-indolinoneYield 26.2%

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent

Conditions

Temperature
50 °C

Procedure

To 15 g aluminum chloride suspended in 30 mL 1,2-dichloroethane in an ice bath was added 7.5 g of 2-oxindole and then 12 g of butanoyl chloride. The resulting suspension was heated to 50° C. overnight. The mixture was poured into ice water and extracted 3 times with ethyl acetate. The combined ethyl acetate layers were washed with brine, dried over sodium sulfate, and concentrated to dryness to give a brown solid. The solid was chromatographed on silica gel (50% ethyl acetate in hexane) to give 3 g (25%) of the title compound as a yellow solid.

Workup

  1. extractionextracted 3 times with ethyl acetate
  2. washThe combined ethyl acetate layers were washed with brine
  3. dry with materialdried over sodium sulfate
  4. concentrationconcentrated to dryness
  5. customto give a brown solid
  6. customThe solid was chromatographed on silica gel (50% ethyl acetate in hexane)

Sources & evidence

ORD record
ord-250ce3e574bd4694b365a1fc0ea0ad6c
Source dataset
uspto-grants-2000_10
Patent number
US06130238

Reaction notes

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