Water → 4-Chloro-5-methyl-1H-indole-2,3-dione

HRID 983532Notes

Reaction equation

HRID 983532 reaction equation
[Cl:1][C:2]1[C:10]([CH3:11])=[CH:9][CH:8]=[C:7]2[C:3]=1[CH:4](SC)[C:5](=[O:12])[NH:6]2.ClN1C(=[O:21])CCC1=O.C1COCC1.O>C(Cl)(Cl)(Cl)Cl>[Cl:1][C:2]1[C:10]([CH3:11])=[CH:9][CH:8]=[C:7]2[C:3]=1[C:4](=[O:21])[C:5](=[O:12])[NH:6]2

Participants

6

Reactant 4

HCID 962WaterHCID 8028TetrahydrofuranHCID 31398ChlorosuccinimideHCID 219059304-Chloro-5-methyl-3-(methylthio)indolin-2-one

Product 1

HCID 225608594-Chloro-5-methyl-1H-indole-2,3-dioneYield 80.9%

Reagents, catalysts & solvents 1

HCID 5943Carbon TetrachlorideSolvent

Procedure

This compound is prepared according to the procedure described in step B of Preparation 1.23, starting with 0.72 g of 4-chloro-5-methyl-3-methylthio-1,3-dihydro-2H-indol-2-one and 0.422 g of N-chloro-succinimide in 72 ml of carbon tetrachloride, and then 58 ml of THF and 14 ml of water. The product obtained is chromatographed on silica gel, eluting with DCM and then with a gradient of a DCM/EtOAc mixture up to (90/10; v/v). 0.5 g of the expected product is obtained.

Workup

  1. customThis compound is prepared
  2. customdescribed in step B of Preparation 1.23
  3. customThe product obtained
  4. customis chromatographed on silica gel
  5. washeluting with DCM

Sources & evidence

ORD record
ord-f6d086a95a9645c9a0aaeb197e4a8f97
Source dataset
uspto-grants-2005_03
Patent number
US06864277B2

Reaction notes

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