Hydrochloric Acid → 5-(Chloroacetyl)-1,3-dihydro-2H-indol-2-one

HRID 2121406Notes

Reaction equation

HRID 2121406 reaction equation
[NH:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[CH2:3][C:2]1=[O:10].[Cl-].[Al+3].[Cl-].[Cl-].[Cl:15][CH2:16][C:17](Cl)=[O:18].Cl>ClC(Cl)C.C(OCC)(=O)C>[Cl:15][CH2:16][C:17]([C:6]1[CH:5]=[C:4]2[C:9](=[CH:8][CH:7]=1)[NH:1][C:2](=[O:10])[CH2:3]2)=[O:18]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 6577Chloroacetyl chlorideHCID 321710OxindoleHCID 6451240Aluminum(III) Chloride

Product 1

HCID 20605765-(Chloroacetyl)-1,3-dihydro-2H-indol-2-oneYield 98%

Reagents, catalysts & solvents 2

HCID 63651,1-DichloroethaneSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
45 °C

Procedure

2-Oxindole (6.7 g) was added to a stirred suspension of 23 g of aluminum chloride in 30 mL of dichloroethane in an ice bath. Chloroacetyl chloride (11.3 g) was slowly added and hydrogen chloride gas was evolved. After ten minutes of stirring, the reaction was warmed at 40 to 50° C. for 1.5 hours. Thin layer chromatography (ethyl acetate, silica gel) showed no remaining starting material. The mixture was cooled to room temperature and poured into ice water. The precipitate was collected by vacuum filtration, washed with water and dried under vacuum to give 10.3 g (98%) of 5-chloroacetyl-2-oxindole as an off-white solid.

Workup

  1. temperatureThe mixture was cooled to room temperature
  2. filtrationThe precipitate was collected by vacuum filtration
  3. washwashed with water
  4. customdried under vacuum

Sources & evidence

ORD record
ord-c214fd78c3bd4b30a3ce9c7b9f28f644
Source dataset
uspto-grants-2004_02
Patent number
US06696448B2

Reaction notes

Loading…