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

HRID 31357Notes

Reaction equation

HRID 31357 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-chlorosuccinimide 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-a3e00b97b8384adb9e456ce4da6926c6
Source dataset
uspto-grants-2008_09
Patent number
US07425566B2

Reaction notes

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