Ammonium Chloride → 3-Benzyl-5-chloro-1,3-dihydro-3-hydroxyindol-2-one

HRID 965535Notes

Reaction equation

HRID 965535 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].[CH2:13]([Mg]Cl)[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1.[Cl-].[NH4+]>C1COCC1.CCOCC>[CH2:13]([C:5]1([OH:12])[C:4]2[C:8](=[CH:9][CH:10]=[C:2]([Cl:1])[CH:3]=2)[NH:7][C:6]1=[O:11])[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1

Participants

6

Reactant 3

HCID 25517Ammonium ChlorideHCID 872035-chloro-1H-indole-2,3-dioneHCID 178418336HCID 178418336, compound

Product 1

HCID 190766193-Benzyl-5-chloro-1,3-dihydro-3-hydroxyindol-2-one

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 8028TetrahydrofuranSolvent

Procedure

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.

Workup

  1. temperatureis cooled to +4° C.
  2. concentrationthe solvents are concentrated under vacuum
  3. extractionThe aqueous phase is extracted with AcOEt
  4. washthe organic phase is washed with a saturated solution of NaCl and with water
  5. dry with materialdried over sodium sulfate
  6. customthe solvent is evaporated off under vacuum

Sources & evidence

ORD record
ord-04c01769497341a8a23262402443fd56
Source dataset
uspto-grants-1998_06
Patent number
US05773612

Reaction notes

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