Potassium Iodide → HCID 59494268, compound

HRID 872028Notes

Reaction equation

HRID 872028 reaction equation
[OH:1][CH2:2][C:3]1[CH:11]=[C:10]2[C:6]([CH2:7][C:8](=[O:12])[NH:9]2)=[CH:5][CH:4]=1.Br[CH2:14][CH2:15][CH2:16][O:17][CH3:18].C(=O)([O-])[O-].[K+].[K+].[I-].[K+]>C(#N)C.O>[OH:1][CH2:2][C:3]1[CH:11]=[C:10]2[C:6]([CH2:7][C:8](=[O:12])[N:9]2[CH2:14][CH2:15][CH2:16][O:17][CH3:18])=[CH:5][CH:4]=1

Participants

7

Reactant 4

HCID 4875Potassium IodideHCID 11430Potassium Carbonate2×HCID 5245511-Bromo-3-methoxypropane2×HCID 57309180HCID 57309180, compound

Product 1

HCID 59494268HCID 59494268, compoundYield 80.4%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6342AcetonitrileSolvent

Procedure

A mixture of 6-(hydroxymethyl)-1,3-dihydro-2H-indol-2-one (150 mg), 1-bromo-3-methoxypropane (211 mg), potassium carbonate (254 mg) and potassium iodide (229 mg) in acetonitrile (6 ml) was refluxed for 15 hours. Further, 1-bromo-3-methoxypropane (70.3 mg) and potassium carbonate (127 mg) were added and the mixture was refluxed for 3 hours. Water was added to the reaction mixture under ice-cooling and the mixture was extracted with ethyl acetate. The organic layer was washed with saturated brine, dried over sodium sulfate and concentrated in vacuo. The resulted residue was purified with a silica gel column chromatography (eluting solvent: chloroform to chloroform/methanol=10/1) to give 6-(hydroxymethyl)-1-(3-methoxypropyl)-1,3-dihydro-2H-indol-2-one (174 mg) as a brown oil.

Workup

  1. temperaturewas refluxed for 15 hours
  2. temperaturethe mixture was refluxed for 3 hours
  3. temperaturecooling
  4. extractionthe mixture was extracted with ethyl acetate
  5. washThe organic layer was washed with saturated brine
  6. dry with materialdried over sodium sulfate
  7. concentrationconcentrated in vacuo
  8. customThe resulted residue was purified with a silica gel column chromatography (eluting solvent: chloroform to chloroform/methanol=10/1)

Sources & evidence

ORD record
ord-eb6030af3ec747fd9f129b7260e74431
Source dataset
uspto-grants-2015_03
Patent number
US08975252B2

Reaction notes

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