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

HRID 555661Notes

Reaction equation

HRID 555661 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].[Cl:15][CH2:16][C:17](Cl)=[O:18].Cl>C(Cl)Cl>[Cl:15][CH2:16][C:17]([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: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-one

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
45 °C

Procedure

Under ice-cooling, aluminum chloride (anhydride) (3.5 equivalents) was suspended in methylene chloride, and oxindole (1 equivalent) was added to this solution while stirring. To this solution, chioroacetyl chloride (2 equivalents) was gradually added dropwise, and after generation of hydrogen chloride gas was stopped, the resulting mixture was stirred for about 10 minutes. Thereafter, the reaction mixture was warmed to 40 to 50° C. and stirred for 2 hours. After cooling, the reaction mixture was poured into ice water and the resulting precipitate was collected by filtration, washed with water and dried, whereby 5-chloroacetylindolin-2-one was obtained. 5-chloroacetylindolin-2-one was dissolved in pyridine and the resulting mixture was heated and stirred at 80 to 90° C. for 3 hours. After cooling, the resulting precipitate was collected by filtration, washed with ethanol several times and dissolved in 2.5 N sodium hydroxide, and the resulting solution was stirred at 70 to 75° C. After cooling, the reaction mixture was acidified with hydrochloric acid and the resulting precipitate was collected by filtration, washed with water and dried, whereby 5-carboxyindolin-2-one was obtained. From the thus obtained 5-carboxyindolin-2-one and diformylfuran, a target compound was obtained in the same manner as in Example 1.

Workup

  1. temperatureUnder ice-cooling
  2. stirringthe resulting mixture was stirred for about 10 minutes
  3. stirringstirred for 2 hours
  4. temperatureAfter cooling
  5. filtrationthe resulting precipitate was collected by filtration
  6. washwashed with water
  7. customdried

Sources & evidence

ORD record
ord-982c6fd655b94492a09609fcd3caea0b
Source dataset
uspto-grants-2011_11
Patent number
US08053461B2

Reaction notes

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