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

HRID 1860927Notes

Reaction equation

HRID 1860927 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 of 4-methyl-2-oxindole was stirred in 50 mL of acetonitrile at room temperature while 3.3 g of N-chlorosuccinimide was added in portions. Trifluoroacetic acid (1 mL) was then added. A white precipitate formed. The suspension was stirred at room temperature for 3 days. 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. customA white precipitate formed
  3. filtrationThe white solid was collected by vacuum filtration
  4. washwashed with a small amount of cold acetone
  5. customdried overnight in a vacuum oven at 40° C.

Sources & evidence

ORD record
ord-6cdb4a7e26ea4ce3a5e9a8bf6327b738
Source dataset
uspto-grants-2003_03
Patent number
US06531502B1

Reaction notes

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