Acetone → 5-Fluoro-3-isopropylidene-1,3-dihydro-indol-2-one
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
Product 1
Reagents, catalysts & solvents 1
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
- temperaturewas heated
- temperatureto reflux for 16 hours
- filtrationThe solid was collected by filtration
- washwashed with methanol (20 mL)
- customdried in vacuo
Sources & evidence
- ORD record
- ord-812991ae89c84fd390eb3e99cbf27e4b
- Source dataset
- uspto-grants-2013_01
- Patent number
- US08354443B2
Reaction notes
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