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

HRID 542608Notes

Reaction equation

HRID 542608 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]>C(=S)=S>[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

5

Reactant 3

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

Product 1

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

Reagents, catalysts & solvents 1

HCID 6348Carbon DisulfideSolvent2×

Procedure

To 95 ml. of carbon disulfide was added 27 g. (0.202 mole) of aluminum chloride, followed by the dropwise addition of a solution of 3 ml. (0.042 mole) of acetyl chloride in 5 ml. of carbon disulfide, with stirring. Stirring was continued for 5 minutes and then 4.4 g. (0.033 mole) of 2-oxindole was added. The resulting mixture was heated under reflux for 4 hours and cooled. The carbon disulfide was removed by decantation and the residue was triturated under water and recovered by filtration. After drying, 3.2 g. of the title compound was obtained, m.p. 225°-227° C.

Workup

  1. temperatureThe resulting mixture was heated
  2. temperatureunder reflux for 4 hours
  3. temperaturecooled
  4. customThe carbon disulfide was removed by decantation
  5. customthe residue was triturated under water
  6. filtrationrecovered by filtration
  7. customAfter drying

Sources & evidence

ORD record
ord-21f640359de3464f90575060dfb89acd
Source dataset
uspto-grants-1987_04
Patent number
US04658037

Reaction notes

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