Acetic Acid → N-(2-Oxo-2,3-dihydro-1H-indol-4-yl)glycine

HRID 1669685Notes

Reaction equation

HRID 1669685 reaction equation
[O:1]=[C:2]1[CH2:10][C:9]2[C:4](=[CH:5][CH:6]=[CH:7][C:8]=2[NH:11][CH2:12][C:13]([O:15]CC2C=CC=CC=2)=[O:14])[NH:3]1.CCOC(C)=O.CC(O)=O>CCO.[Pd]>[O:1]=[C:2]1[CH2:10][C:9]2[C:4](=[CH:5][CH:6]=[CH:7][C:8]=2[NH:11][CH2:12][C:13]([OH:15])=[O:14])[NH:3]1

Participants

6

Reactant 3

HCID 176Acetic AcidHCID 8857Ethyl AcetateHCID 66813100Benzyl N-(2-oxo-2,3-dihydro-1H-indol-4-yl)glycinate

Product 1

HCID 59322832N-(2-Oxo-2,3-dihydro-1H-indol-4-yl)glycine

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

A mixture of 10% Pd/C (100 mg) and benzyl N-(2-oxo-2,3-dihydro-1H-indol-4-yl)glycinate from Step C (320 mg, 1.08 mmol) was stirred vigorously in EtOH (5 mL), EtOAc (5 mL), and AcOH (1 mL) under an atmosphere of hydrogen (ca. 1 atm). After 4 h, the mixture was filtered through a pad of Celite, washing with MeOH, and the filtrate was concentrated to give the title compound. MS: m/z=207 (M+1).

Workup

  1. filtrationthe mixture was filtered through a pad of Celite
  2. washwashing with MeOH
  3. concentrationthe filtrate was concentrated

Sources & evidence

ORD record
ord-a0617c25583c42dcb0e16982a88fa609
Source dataset
uspto-grants-2011_08
Patent number
US07989624B2

Reaction notes

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