Phenylmethyl 2,3-dihydro-1-methyl-2-oxo-1H-indole-5-carboxylate → 2,3-Dihydro-1-methyl-2-oxo-1H-indole-5-carboxylic acid

HRID 1976781Notes

Reaction equation

HRID 1976781 reaction equation
[CH3:1][N:2]1[C:10]2[C:5](=[CH:6][C:7]([C:11]([O:13]CC3C=CC=CC=3)=[O:12])=[CH:8][CH:9]=2)[CH2:4][C:3]1=[O:21]>C(OCC)(=O)C.CO.[Pd]>[CH3:1][N:2]1[C:10]2[C:5](=[CH:6][C:7]([C:11]([OH:13])=[O:12])=[CH:8][CH:9]=2)[CH2:4][C:3]1=[O:21]

Participants

5

Reactant 1

HCID 21998744Phenylmethyl 2,3-dihydro-1-methyl-2-oxo-1H-indole-5-carboxylate

Product 1

HCID 219987472,3-Dihydro-1-methyl-2-oxo-1H-indole-5-carboxylic acidYield 56.3%

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 887MethanolSolventHCID 8857Ethyl AcetateSolvent

Procedure

A solution of Example 59A (1.2 g, 4.27 mmol) in ethyl acetate (30 mL) and methanol (20 mL) was treated with 10% Pd/C (200 mg), stirred under hydrogen (balloon) for 18 hours, filtered through diatomaceous earth (Celite®) with 9:1 dichloromethane/methanol solution rinses, and concentrated to provide 460 mg of the desired product.

Workup

  1. filtrationfiltered through diatomaceous earth (Celite®) with 9:1 dichloromethane/methanol solution rinses
  2. concentrationconcentrated

Sources & evidence

ORD record
ord-46869cd61e5d4451b0eb5d2da6041cd9
Source dataset
uspto-grants-2001_05
Patent number
US06228868B1

Reaction notes

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