Ethyl Acetate → Oxindole

HRID 2200163Notes

Reaction equation

HRID 2200163 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[CH2:8][C:9]([O:11]C)=O.C(=O)([O-])[O-].[K+].[K+].CCOC(C)=O>CN(C=O)C>[NH:1]1[C:2]2[C:3](=[CH:4][CH:5]=[CH:6][CH:7]=2)[CH2:8][C:9]1=[O:11]

Participants

5

Reactant 3

HCID 8857Ethyl AcetateHCID 11430Potassium CarbonateHCID 5743389Methyl 2-aminobenzeneacetate

Product 1

HCID 321710OxindoleYield 103.2%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Stir the mixture of methyl 2-(2-aminophenyl)acetate (4.8 g, 29.1 mmol) and potassium carbonate (8.0 g, 58.2 mmol) in DMF (15 mL) at room temperature overnight. TLC (PE:EtOAc=2:1) shows the reaction is complete. Concentrate the reaction mixture under reduced pressure to give the crude product. Purify by chromatography (silica gel, EtOAc:PE=1:2) to afford the title compound (4.0 g, 95%). MS: (M+1): 134.2.

Workup

  1. concentrationConcentrate the reaction mixture under reduced pressure
  2. customto give the crude product
  3. customPurify by chromatography (silica gel, EtOAc:PE=1:2)

Sources & evidence

ORD record
ord-f3e2deffdc0f437594992f3d0f7fcf49
Source dataset
uspto-grants-2016_06
Patent number
US09359338B2

Reaction notes

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