Ammonium Chloride → 5-Chloro-3-(cyclohexylmethyl)-1,3-dihydro-3-hydroxyindol-2-one

HRID 234485Notes

Reaction equation

HRID 234485 reaction equation
[Mg:1].[Br:2][CH2:3][CH:4]1[CH2:9][CH2:8][CH2:7][CH2:6][CH2:5]1.[Cl:10][C:11]1[CH:12]=[C:13]2[C:17](=[CH:18][CH:19]=1)[NH:16][C:15](=[O:20])[C:14]2=[O:21].[Cl-].[NH4+]>CCOCC.C1COCC1>[CH:13]1([CH2:14][Mg:1][Br:2])[CH2:17][CH2:18][CH2:19][CH2:11][CH2:12]1.[Cl:10][C:11]1[CH:12]=[C:13]2[C:17](=[CH:18][CH:19]=1)[NH:16][C:15](=[O:20])[C:14]2([CH2:3][CH:4]1[CH2:9][CH2:8][CH2:7][CH2:6][CH2:5]1)[OH:21]

Participants

8

Reactant 4

HCID 25517Ammonium ChlorideHCID 872035-chloro-1H-indole-2,3-dioneHCID 137636Cyclohexane, (bromomethyl)-HCID 5462224Magnesium

Product 2

HCID 190763805-Chloro-3-(cyclohexylmethyl)-1,3-dihydro-3-hydroxyindol-2-oneHCID 178419664HCID 178419664, compound

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 8028TetrahydrofuranSolvent

Procedure

A solution of cyclohexylmethylmagnesium bromide is prepared from 5.37 g of magnesium and 30.8 ml of bromomethylcyclohexane in 15 ml of ether. This solution is added dropwise at +4° C., under an argon atmosphere, to a mixture of 10 g of 5-chloroisatin and 25 ml of THF. After stirring for 3 hours at RT, 500 ml of a saturated solution of ammonium chloride are added, extraction is carried out 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 12 g of the expected product after crystallization from AcOEt and recrystallization from a THF/AcOEt mixture. M.p.=252°-253° C. (dec.).

Workup

  1. extractionextraction
  2. washthe organic phase is washed with a saturated solution of NaCl and with water
  3. dry with materialdried over sodium sulfate
  4. customthe solvent is evaporated off under vacuum

Sources & evidence

ORD record
ord-13e5669f3241483f99e27d35d12ee59f
Source dataset
uspto-grants-1997_01
Patent number
US05594023

Reaction notes

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