Sodium Hydroxide → HCID 58437451, compound

HRID 1258226Notes

Reaction equation

HRID 1258226 reaction equation
[CH:1]([C:3]1[O:7][C:6]([N:8]2[C:16]3[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=3)[C:10]([C:17]#[N:18])=[CH:9]2)=[CH:5][CH:4]=1)=[O:2].[OH-:19].[Na+]>CO.O1CCCC1.[Ag]=O>[C:17]([C:10]1[C:11]2[C:16](=[CH:15][CH:14]=[CH:13][CH:12]=2)[N:8]([C:6]2[O:7][C:3]([C:1]([OH:19])=[O:2])=[CH:4][CH:5]=2)[CH:9]=1)#[N:18]

Participants

6

Reactant 2

HCID 14798Sodium HydroxideHCID 584373031-(5-Formylfuran-2-yl)-1H-indole-3-carbonitrile

Product 1

HCID 58437451HCID 58437451, compound

Reagents, catalysts & solvents 3

HCID 92152Silver(II) oxideCatalystHCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a suspension of 1-(5-formylfuran-2-yl)-1H-indole-3-carbonitrile (0.085 g) in methanol (4 mL) and tetrahydrofuran (4 mL) were added silver oxide (0.1 g) and 2 mol/L aqueous sodium hydroxide solution (0.27 mL), this mixture was stirred at room temperature for 6 hours. The insoluble material of reaction mixture was removed by filtration, and the filtrate was concentrated under reduced pressure. To this residue were added water (15 mL) and 2 mol/L hydrochloric acid solution (2 mL), this mixture was extracted with ethyl acetate. This organic layer was washed with brine, dried over anhydrous magnesium sulfate. The solvent was removed under reduced pressure. The residue was purified by column chromatography on silica gel (eluent: dichloromethane/methanol=10/1) to give the title compound (0.023 g).

Workup

  1. customThe insoluble material of reaction mixture
  2. customwas removed by filtration
  3. concentrationthe filtrate was concentrated under reduced pressure
  4. additionTo this residue were added water (15 mL) and 2 mol/L hydrochloric acid solution (2 mL)
  5. extractionthis mixture was extracted with ethyl acetate
  6. washThis organic layer was washed with brine
  7. dry with materialdried over anhydrous magnesium sulfate
  8. customThe solvent was removed under reduced pressure
  9. customThe residue was purified by column chromatography on silica gel (eluent: dichloromethane/methanol=10/1)

Sources & evidence

ORD record
ord-f3fbf87029734ef9bb915b0b82bc5722
Source dataset
uspto-grants-2013_06
Patent number
US08466152B2

Reaction notes

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