Hydrazine hydrate (1:1) → 1-Ethyl-7-fluoro-1,3-dihydro-indol-2-one

HRID 2114878Notes

Reaction equation

HRID 2114878 reaction equation
[CH2:1]([N:3]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][C:10]=2[F:12])[C:5](=O)[C:4]1=[O:14])[CH3:2].O.NN>>[CH2:1]([N:3]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][C:10]=2[F:12])[CH2:5][C:4]1=[O:14])[CH3:2]

Participants

3

Reactant 2

HCID 24654Hydrazine hydrate (1:1)HCID 692740961-Ethyl-7-fluoroindoline-2,3-dione

Product 1

HCID 692741661-Ethyl-7-fluoro-1,3-dihydro-indol-2-one

Procedure

1-Ethyl-7-fluoro-1H-indole-2,3-dione (3.60 g, 18.6 mmol) is heated with neat hydrazine hydrate (15 ml) at 130° C. for 60 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 an orange solid. HPLC r.t. 4.60 min; MS for C10H10FNO 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-874f48d9ff134c66b85b11ac059663fc
Source dataset
uspto-grants-2008_10
Patent number
US07435751B2

Reaction notes

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