Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Ethyl Acetate | HCID 8857 | — |
| Reactant | Sodium hydride | HCID 24758 | — |
| Reactant | Ammonium Chloride | HCID 25517 | — |
| Reactant | 5-chloro-1H-indole-2,3-dione | HCID 87203 | — |
| Solvent | Tetrahydrofuran | HCID 8028 | — |
| Product | HCID 86625721 | HCID 86625721 | — |
Reaction Steps
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).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US08030499B2 |
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| Source dataset | uspto-grants-2011_10 |
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| ORD ID | ord-3652fdb1195448d8a62234f8edb22247 |
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| Source note | uspto-grants-2011_10 |
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