1,3-Dimethoxybenzene → HCID 22560894, compound

HRID 1662775Notes

Reaction equation

HRID 1662775 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][CH:6]=[C:5]([O:9][CH3:10])[CH:4]=1.C([Li])CCC.[Cl:16][C:17]1[CH:18]=[C:19]2[C:23](=[CH:24][CH:25]=1)[NH:22][C:21](=[O:26])[C:20]2=[O:27].[NH4+].[Cl-]>C1COCC1.CCCCCC>[Cl:16][C:17]1[CH:18]=[C:19]2[C:23](=[CH:24][CH:25]=1)[NH:22][C:21](=[O:26])[C:20]2([C:4]1[C:3]([O:2][CH3:1])=[CH:8][CH:7]=[CH:6][C:5]=1[O:9][CH3:10])[OH:27]

Participants

7

Reactant 4

HCID 90251,3-DimethoxybenzeneHCID 25517Ammonium ChlorideHCID 872035-chloro-1H-indole-2,3-dioneHCID 178418339Butyllithium

Product 1

HCID 22560894HCID 22560894, compoundYield 80.6%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8058HexaneSolvent

Procedure

Under nitrogen atmosphere, to a solution of 22.8 g of 1,3-dimethoxy benzene in THF (150 ml) was added dropwise a solution of 1.59 mol/L n-butyl lithium in an n-hexane solution (104 ml) over 30 minutes under ice cooling, and the reaction mixture was stirred at room temperature for one hour. The solution was cooled by ice again, 10.0 g of 5-chloroisatin and was added, and the reaction mixture was stirred at room temperature for two hours. An aqueous solution of saturated NH4Cl was added to the solution and the resulting mixture was extracted with EtOAc; the organic layer was washed with saturated brine and dried over Na2SO4, 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 60N; mobile phase: CHCl3/MeOH=50/1 to 10/1; v/v) to obtain 14.2 g of the title compound.

Workup

  1. temperatureThe solution was cooled by ice again
  2. stirringthe reaction mixture was stirred at room temperature for two hours
  3. extractionthe resulting mixture was extracted with EtOAc
  4. washthe organic layer was washed with saturated brine
  5. dry with materialdried over Na2SO4
  6. customthe drying agent was separated by filtration
  7. customthe solvent was evaporated under reduced pressure
  8. customThe obtained residue was purified by column chromatography (silicagel 60N; mobile phase: CHCl3/MeOH=50/1 to 10/1; v/v)

Sources & evidence

ORD record
ord-a80a2e9962464d99b1127bc39ac16bb1
Source dataset
uspto-grants-2011_10
Patent number
US08030499B2

Reaction notes

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