Ethyl Acetate → HCID 86625721, compound

HRID 1662774Notes

Reaction equation

HRID 1662774 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[NH:7][C:6](=[O:11])[C:5]2=[O:12].[H-].[Na+].[NH4+:15].[Cl-].C[CH2:18][O:19][C:20]([CH3:22])=O>C1COCC1>[Cl:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[NH:7][C:6](=[O:11])[C:5]2([C:2]1[CH:3]=[C:4]([CH:5]=[CH:22][C:20]=1[O:19][CH3:18])[C:8]#[N:15])[OH:12]

Participants

6

Reactant 4

HCID 8857Ethyl AcetateHCID 24758Sodium hydrideHCID 25517Ammonium ChlorideHCID 872035-chloro-1H-indole-2,3-dione

Product 1

HCID 86625721HCID 86625721, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Under nitrogen atmosphere, to a suspension of 3.57 g of 5-chloroisatin in THF (100 ml) was added 865 mg of NaH under ice cooling and the reaction mixture was stirred for one hour. Thereafter, the solution prepared beforehand was added dropwise. The solution was stirred at the same temperature for two hours, then, a saturated aqueous solution of NH4Cl and EtOAc were added and liquid separation was performed; the organic layer was washed with saturated brine and dried over MgSO4, then, the drying agent was separated by filtration and the solvent was evaporated under reduced pressure. The obtained residue was purified by column chromatography (silicagel 60; mobile phase: EtOAc/n-hexane=1/1 to MeOH/CHCl3=1/9; v/v) to obtain 460 mg of the title compound (colorless solid).

Workup

  1. customThereafter, the solution prepared beforehand
  2. additionwas added dropwise
  3. stirringThe solution was stirred at the same temperature for two hours
  4. customliquid separation
  5. washthe organic layer was washed with saturated brine
  6. dry with materialdried over MgSO4
  7. customthe drying agent was separated by filtration
  8. customthe solvent was evaporated under reduced pressure
  9. customThe obtained residue was purified by column chromatography (silicagel 60; mobile phase: EtOAc/n-hexane=1/1 to MeOH/CHCl3=1/9; v/v)

Sources & evidence

ORD record
ord-3652fdb1195448d8a62234f8edb22247
Source dataset
uspto-grants-2011_10
Patent number
US08030499B2

Reaction notes

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