5-(Hydroxymethyl)-1,3-Dihydro-2H-Indol-2-One → 2,3-Dihydro-2-oxo-1H-indole-5-carboxaldehyde

HRID 748527Notes

Reaction equation

HRID 748527 reaction equation
[OH:1][CH2:2][C:3]1[CH:4]=[C:5]2[C:9](=[CH:10][CH:11]=1)[NH:8][C:7](=[O:12])[CH2:6]2>N1C=CC=CC=1.[O-2].[Cr+6].[O-2].[O-2]>[O:12]=[C:7]1[CH2:6][C:5]2[C:9](=[CH:10][CH:11]=[C:3]([CH:2]=[O:1])[CH:4]=2)[NH:8]1

Participants

4

Reactant 1

HCID 597510365-(Hydroxymethyl)-1,3-Dihydro-2H-Indol-2-One

Product 1

HCID 597510372,3-Dihydro-2-oxo-1H-indole-5-carboxaldehydeYield 46.5%

Reagents, catalysts & solvents 2

HCID 10219390chromium (VI) trioxideCatalystHCID 1049PyridineSolvent3×

Procedure

Chromium(VI) oxide (240 mg, 2.4 mmol) was added to ice-cooled pyridine (3 mL). To the formed yellow suspension was added additional pyridine (2 mL) and 5-(hydroxymethyl)-1,3-dihydro-2H-indol-2-one (130 mg, 0.8 mmol) dissolved in pyridine (3 mL). The reaction was quenched after 15 min by the addition of water (50 mL) and extracted with ethyl acetate. The organic phases were dried (Na2SO4) and evaporated in vacuo. The crude product was purified on a silica gel column using methylene chloride/methanol, (10:1), as the eluent to give 60 mg (46% yield) of the title compound.

Workup

  1. customThe reaction was quenched after 15 min by the addition of water (50 mL)
  2. extractionextracted with ethyl acetate
  3. dry with materialThe organic phases were dried (Na2SO4)
  4. customevaporated in vacuo
  5. customThe crude product was purified on a silica gel column

Sources & evidence

ORD record
ord-73aaf4bb5c9b4022bdddf3a66a66430b
Source dataset
uspto-grants-2008_07
Patent number
US07399780B2

Reaction notes

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