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

HRID 2087037Notes

Reaction equation

HRID 2087037 reaction equation
[Al+3].[Cl-].[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:17])[CH3:16]>CN(C=O)C>[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:17])[CH3:16]

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 6228DimethylformamideSolvent

Procedure

AlCl3 (303 g, 2.27 mol) is placed in a 3-necked flask fitted with a thermometer and a dropping funnel. While stirring DMF (50 ml) is added dropwise and the temperature rises to about 60°. The mixture is cooled down to 45°, and oxindole (33 g, 0.25 mol) is added in 3 portions. After an additional 10 minutes, acetyl chloride (36 ml, 0.5 mol) is added. The mixture is stirred for an additional 30 minutes at room temperature. The mixture is poured onto ice (3000 g). This results in the formation of a solid which is filtered off, washed first with water and then with cold methanol (1000 ml), and then dried to give 5-acetyloxindole.

Workup

  1. customfitted with a thermometer and a dropping funnel
  2. additionis added dropwise
  3. customrises to about 60°
  4. temperatureThe mixture is cooled down to 45°
  5. additionThe mixture is poured onto ice (3000 g)
  6. customThis results in the formation of a solid which
  7. filtrationis filtered off
  8. washwashed first with water
  9. dry with materialwith cold methanol (1000 ml), and then dried

Sources & evidence

ORD record
ord-3dc0dfbedf994e8cbaf0527a213905c2
Source dataset
uspto-grants-2004_04
Patent number
US06727281B2

Reaction notes

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