Hydrogen Peroxide → 1-Oxo-indan-5-carboxylic acid amide

HRID 1690682Notes

Reaction equation

HRID 1690682 reaction equation
[O:1]=[C:2]1[C:10]2[C:5](=[CH:6][C:7]([C:11]#[N:12])=[CH:8][CH:9]=2)[CH2:4][CH2:3]1.[OH:13]O>[OH-].[K+]>[O:1]=[C:2]1[C:10]2[C:5](=[CH:6][C:7]([C:11]([NH2:12])=[O:13])=[CH:8][CH:9]=2)[CH2:4][CH2:3]1

Participants

4

Reactant 2

HCID 784Hydrogen PeroxideHCID 3128961-oxo-2,3-dihydro-1H-indene-5-carbonitrile

Product 1

HCID 108211341-Oxo-indan-5-carboxylic acid amide

Reagents, catalysts & solvents 1

HCID 14797Potassium HydroxideSolvent

Procedure

To a suspension of 1-oxo-indan-5-carbonitrile (100 mg, 0.64 mmol) in KOH (25%, 0.21 mL) at 0° C., is added H2O2 (0.32 mL). The mixture is stirred at rt for 30 min, then at 50° C. for 1 h. After cooling to room temperature, the mixture is extracted with EtOAc (3×10 mL). The combined organic phases are washed with brine and dried over Na2SO4. Evaporation of the solvent affords 1-oxo-indan-5-carboxylic acid amide as a white solid. Aqueous HCl (4N, 3 mL) is added to the solid. The mixture is heated to 90° C. for 2 h. Then the reaction mixture is extracted with EtOAc (3×10 mL). The combined organic phasea are washed with brine. MeOH (5 mL) is added to the solution, followed by trimethylsilyldiazomethane (2M in ether) dropwise until all the carboxylic acid was consumed. Evaporation of solvent affords crude product, 1-oxo-indan-5-carboxylic acid methyl ester, which is pure enough for the next step. ESMS m/z 191.1 (M+H+).

Workup

  1. waitat 50° C. for 1 h
  2. temperatureAfter cooling to room temperature
  3. extractionthe mixture is extracted with EtOAc (3×10 mL)
  4. washThe combined organic phases are washed with brine
  5. dry with materialdried over Na2SO4
  6. customEvaporation of the solvent

Sources & evidence

ORD record
ord-c82a771562ba4776bd83bc4db401edba
Source dataset
uspto-grants-2012_04
Patent number
US08153671B2

Reaction notes

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