Ammonium Chloride → 5-Chloro-3-cyclohexyl-1,3-dihydro-3-hydroxyindol-2-one

HRID 234484

Reaction equation

HRID 234484 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].[CH:13]1([Mg]Cl)[CH2:18][CH2:17][CH2:16][CH2:15][CH2:14]1.[Cl-].[NH4+]>C1COCC1.CCOCC>[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([CH:13]1[CH2:18][CH2:17][CH2:16][CH2:15][CH2:14]1)[OH:12]

Participants

6

Reactant 3

HCID 25517Ammonium ChlorideHCID 872035-chloro-1H-indole-2,3-dioneHCID 178478990HCID 178478990, compound

Product 1

HCID 190763685-Chloro-3-cyclohexyl-1,3-dihydro-3-hydroxyindol-2-one

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 8028TetrahydrofuranSolvent

Procedure

A suspension of 18.15 g of 5-chloroisatin in 45 ml of THF is cooled to +4° C., 200 ml of a 2M solution of cyclohexylmagnesium chloride in ether are added dropwise and the mixture is stirred for 3 hours at RT. 900 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 dried over sodium sulfate and the solvent is evaporated off under vacuum to give 4 g of the expected product after crystallization from a THF/AcOEt mixture.

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
  5. dry with materialdried over sodium sulfate
  6. customthe solvent is evaporated off under vacuum

Sources & evidence

ORD record
ord-9afa5621564446e39dc58e7de1185cfd
Source dataset
uspto-grants-1997_01
Patent number
US05594023

Linked notes

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