Trifluoroacetic acid → 5-Chloro-4-methylindolin-2-one

HRID 1815426Notes

Reaction equation

HRID 1815426 reaction equation
[CH3:1][C:2]1[CH:10]=[CH:9][CH:8]=[C:7]2[C:3]=1[CH2:4][C:5](=[O:11])[NH:6]2.[Cl:12]N1C(=O)CCC1=O.FC(F)(F)C(O)=O>C(#N)C>[Cl:12][C:10]1[C:2]([CH3:1])=[C:3]2[C:7](=[CH:8][CH:9]=1)[NH:6][C:5](=[O:11])[CH2:4]2

Participants

5

Reactant 3

HCID 6422Trifluoroacetic acidHCID 31398ChlorosuccinimideHCID 125793824-Methyl-1,3-dihydro-2H-indol-2-one

Product 1

HCID 103133885-Chloro-4-methylindolin-2-oneYield 68%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A suspension of 3.0 g 4-methyl-2-oxindole was stirred in 50 mL acetonitrile at room temperature while 3.3 g of N-chloro-succinimide was added in portions. Trifluoroacetic acid (1 mL) was then added. The suspension was stirred at room temperature for 3 days during which time solids were always present. The white solid was collected by vacuum filtration, washed with a small amount of cold acetone and dried overnight in a vacuum oven at 40° C. to give 2.5 g (68%) of 5-chloro-4-methyl-2-oxindole.

Workup

  1. additionwas added in portions
  2. filtrationThe white solid was collected by vacuum filtration
  3. washwashed with a small amount of cold acetone
  4. customdried overnight in a vacuum oven at 40° C.

Sources & evidence

ORD record
ord-4eb9108db53945ac9118285c82cc823d
Source dataset
uspto-grants-2005_04
Patent number
US06878733B1

Reaction notes

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