Acetone → 5-Fluoro-3-isopropylidene-1,3-dihydro-indol-2-one

HRID 1805357Notes

Reaction equation

HRID 1805357 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])[CH2:5]2.[CH3:12][C:13]([CH3:15])=O.N1CCCCC1>CO>[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=[C:13]([CH3:15])[CH3:12]

Participants

5

Reactant 3

HCID 180AcetoneHCID 8082PiperidineHCID 37310125-fluoro-1,3-dihydro-2H-indol-2-one

Product 1

HCID 672305505-Fluoro-3-isopropylidene-1,3-dihydro-indol-2-oneYield 68%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A mixture of 5-fluoro-1,3-dihydro-indol-2-one (2.84 g, 20 mmol), acetone (2.2 mL, 30 mmol) and piperidine (0.8 mL, 8 mmol) in methanol (100 mL) was heated to reflux for 16 hours. Then the reaction mixture was allowed to cool to room temperature. The solid was collected by filtration, washed with methanol (20 mL) and dried in vacuo to afford 5-fluoro-3-isopropylidene-1,3-dihydro-indol-2-one (2.6 g, 68%) as powder.

Workup

  1. temperaturewas heated
  2. temperatureto reflux for 16 hours
  3. filtrationThe solid was collected by filtration
  4. washwashed with methanol (20 mL)
  5. customdried in vacuo

Sources & evidence

ORD record
ord-812991ae89c84fd390eb3e99cbf27e4b
Source dataset
uspto-grants-2013_01
Patent number
US08354443B2

Reaction notes

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