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

HRID 1358477Notes

Reaction equation

HRID 1358477 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 stage B of Preparation 1.10 from 0.72 g of 4-chloro-5-methyl-3-methylthio-1,3-dihydro-2H-indol-2-one and 0.422 g of N-chlorosuccinimide in 72 ml of carbon tetrachloride and then from 58 ml of THF and 14 ml of water. The product obtained is chromatographed on silica gel, elution being carried out with DCM and then with the gradient of the DCM/AcOEt mixture up to (90/10, v/v). 0.5 g of the expected product is obtained.

Workup

  1. customThis compound is prepared
  2. customThe product obtained
  3. customis chromatographed on silica gel, elution

Sources & evidence

ORD record
ord-089851175b4f43688e6648d1ecc71ad6
Source dataset
uspto-grants-2003_07
Patent number
US06596732B2

Reaction notes

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