5-Fluoroisatin → 5-fluoro-1,3-dihydro-2H-indol-2-one

HRID 731139Notes

Reaction equation

HRID 731139 reaction equation
[F:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[NH:7][C:6](=[O:11])[C:5]2=O>O.NN>[F:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[NH:7][C:6](=[O:11])[CH2:5]2

Participants

3

Reactant 1

HCID 2365665-Fluoroisatin

Product 1

HCID 37310125-fluoro-1,3-dihydro-2H-indol-2-oneYield 99.8%

Reagents, catalysts & solvents 1

HCID 24654Hydrazine hydrate (1:1)Solvent

Procedure

5-Fluoroisatin (8.2 g, 49.7 mmol) was dissolved in 50 mL of hydrazine hydrate and refluxed for 1 hour. The reaction mixtures were then poured in ice water. The precipitate was then filtered, washed with water and dried under vacuum oven to give 5-fluoro-2-oxindole (7.5 g).

Workup

  1. temperaturerefluxed for 1 hour
  2. customThe reaction mixtures
  3. filtrationThe precipitate was then filtered
  4. washwashed with water
  5. customdried under vacuum oven

Sources & evidence

ORD record
ord-4c216624da1f4c72a2e747cc14662ba0
Source dataset
uspto-grants-2009_09
Patent number
US07582756B2

Reaction notes

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