2-Methoxy-6-nitrophenylacetic acid → 4-Methoxy-2-indolinone

HRID 1634721Notes

Reaction equation

HRID 1634721 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][CH:6]=[C:5]([N+:9]([O-])=O)[C:4]=1[CH2:12][C:13]([OH:15])=O>[Pd].C(O)(=O)C>[CH3:1][O:2][C:3]1[CH:8]=[CH:7][CH:6]=[C:5]2[C:4]=1[CH2:12][C:13](=[O:15])[NH:9]2

Participants

4

Reactant 1

HCID 5643152-Methoxy-6-nitrophenylacetic acid

Product 1

HCID 5960014-Methoxy-2-indolinoneYield 36.8%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 176Acetic AcidSolvent

Procedure

A mixture of 2-methoxy-6-nitrophenylacetic acid (31 g, 150 mmol), and 3.0 g of 10% palladium on carbon in 200 mL of glacial acetic acid was stirred under an atmosphere of H2 gas until uptake ceased. The catalyst was filtered and the solvent evaporated in vacuo. The crude product was crystallized from methanol to give 9.0 g of the title compound.

Workup

  1. filtrationThe catalyst was filtered
  2. customthe solvent evaporated in vacuo
  3. customThe crude product was crystallized from methanol

Sources & evidence

ORD record
ord-70dd1cf5d8894f15bdad729350d42a10
Source dataset
uspto-grants-2003_01
Patent number
US06506901B2

Reaction notes

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