HuagongsheHuagongshe Chemistry Print Report · For research reference only
Ammonium Chloride → 3-Benzyl-5-chloro-1,3-dihydro-3-hydroxyindol-2-one
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Ammonium Chloride | HCID 25517 | — |
| Reactant | 5-chloro-1H-indole-2,3-dione | HCID 87203 | — |
| Reactant | HCID 178418336 | HCID 178418336 | — |
| Solvent | Diethyl Ether | HCID 3283 | — |
| Solvent | Tetrahydrofuran | HCID 8028 | — |
| Product | 3-Benzyl-5-chloro-1,3-dihydro-3-hydroxyindol-2-one | HCID 19076619 | — |
Reaction Steps
A suspension of 10 g of 5-chloroisatin in 150 ml of THF is cooled to +4° C., 220 ml of a 1M solution of benzylmagnesium chloride in ether are added dropwise and the mixture is stirred for 3 hours at RT. 500 ml of a saturated solution of ammonium chloride are added and the solvents are concentrated under vacuum. The aqueous phase is extracted with AcOEt, the organic phase is washed with a saturated solution of NaCl and with water and dried over sodium sulfate and the solvent is evaporated off under vacuum to give 5.6 g of the expected product after crystallization from a THF/AcOEt mixture. M.p.=204°-205° C.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US05773612 |
| Source dataset | uspto-grants-1998_06 |
| ORD ID | ord-04c01769497341a8a23262402443fd56 |
| Source note | uspto-grants-1998_06 |