7-Fluoro-1-(2-fluoroethyl)indoline-2,3-dione → 7-Fluoro-1-(2-fluoro-ethyl)-1,3-dihydro-indol-2-one

HRID 2114885Notes

Reaction equation

HRID 2114885 reaction equation
[F:1][C:2]1[CH:3]=[CH:4][CH:5]=[C:6]2[C:10]=1[N:9]([CH2:11][CH2:12][F:13])[C:8](=[O:14])[C:7]2=O>O.NN>[F:1][C:2]1[CH:3]=[CH:4][CH:5]=[C:6]2[C:10]=1[N:9]([CH2:11][CH2:12][F:13])[C:8](=[O:14])[CH2:7]2

Participants

3

Reactant 1

HCID 739475787-Fluoro-1-(2-fluoroethyl)indoline-2,3-dione

Product 1

HCID 739475797-Fluoro-1-(2-fluoro-ethyl)-1,3-dihydro-indol-2-one

Reagents, catalysts & solvents 1

HCID 24654Hydrazine hydrate (1:1)Solvent

Procedure

7-Fluoro-1-(2-fluoro-ethyl)-1H-indole-2,3-dione (1.04 g, 4.92 mmol) is heated with neat hydrazine hydrate (10 ml) at 130° C. for 20 minutes. The mixture is cooled, diluted with ice water and extracted with ethyl acetate. The extract is washed with brine, dried (Na2SO4), and evaporated to give the title compound as a brown solid. HPLC r.t. 4.36 min; MS for C10H9F2NO m/z 198.1 (M+H)+.

Workup

  1. temperatureThe mixture is cooled
  2. extractionextracted with ethyl acetate
  3. washThe extract is washed with brine
  4. dry with materialdried (Na2SO4)
  5. customevaporated

Sources & evidence

ORD record
ord-5bfc516fcc2c46f9bdc26ad529cf186c
Source dataset
uspto-grants-2008_10
Patent number
US07435751B2

Reaction notes

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