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

HRID 1860853Notes

Reaction equation

HRID 1860853 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>[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

6

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 1

HCID 63651,1-DichloroethaneSolvent

Conditions

Temperature
45 °C

Procedure

2-Oxindole (6.7 g) was added to a suspension of aluminum chloride (23 g) in dichloroethane (30 ml) cooled 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 to 40-50° C. for 1.5 hours. 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. temperaturecooled in an ice bath
  2. temperatureThe mixture was cooled to room temperature
  3. filtrationThe precipitate was collected by vacuum filtration
  4. washwashed with water
  5. customdried under vacuum

Sources & evidence

ORD record
ord-76cc00804abc48d0a7b4c45498e93d13
Source dataset
uspto-grants-2003_03
Patent number
US06531502B1

Reaction notes

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