5-Fluoro-2-nitrophenylacetic acid → 5-fluoro-1,3-dihydro-2H-indol-2-one

HRID 971426Notes

Reaction equation

HRID 971426 reaction equation
[F:1][C:2]1[CH:3]=[CH:4][C:5]([N+:12]([O-])=O)=[C:6]([CH2:8][C:9](O)=[O:10])[CH:7]=1.[H][H]>[Pt]=O>[F:1][C:2]1[CH:7]=[C:6]2[C:5](=[CH:4][CH:3]=1)[NH:12][C:9](=[O:10])[CH2:8]2

Participants

4

Reactant 2

HCID 103978545-Fluoro-2-nitrophenylacetic acidHCID 178418361HCID 178418361, compound

Product 1

HCID 37310125-fluoro-1,3-dihydro-2H-indol-2-one

Reagents, catalysts & solvents 1

HCID 82844Platinum oxide (PtO)Catalyst

Procedure

A mixture of 24 g. of 5-fluoro-2-nitro-phenylacetic acid, 2.0 g. of platinum oxide (PtO2) and 250 ml. of glacial acid is hydrogenated at room temperature and 50 p.s.i. until the theoretical amount of hydrogen is taken up. The resulting mixture is filtered and the solvent evaporated off in vacuo. The residue is triturated with water and the resulting precipitate recrystallized from methylene chloride/diethyl ether to obtain 5-fluoro-oxindole, m.p. 131°-133° C.

Workup

  1. additionA mixture of 24 g
  2. customis hydrogenated at room temperature
  3. filtrationThe resulting mixture is filtered
  4. customthe solvent evaporated off in vacuo
  5. customThe residue is triturated with water
  6. customthe resulting precipitate recrystallized from methylene chloride/diethyl ether

Sources & evidence

ORD record
ord-c9d8d3d5f90541a2827b5a038782e971
Source dataset
uspto-grants-1979_07
Patent number
US04160032

Reaction notes

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