1-(2,2,2-Trifluoroacetyl)indoline-5-carbonitrile → 2,3-Dihydro-1H-indole-5-carbonitrile
Reaction equation
FC(F)(F)C([N:5]1[C:13]2[C:8](=[CH:9][C:10]([C:14]#[N:15])=[CH:11][CH:12]=2)[CH2:7][CH2:6]1)=O>C1COCC1.[OH-].[Na+]>[NH:5]1[C:13]2[C:8](=[CH:9][C:10]([C:14]#[N:15])=[CH:11][CH:12]=2)[CH2:7][CH2:6]1Participants
4
Reactant 1
Product 1
Reagents, catalysts & solvents 2
Procedure
1-(2,2,2-Trifluoroacetyl)-2,3-dihydro-1H-indole-5-carbonitrile (13 g, 0.0542 mol; see step (iii) above) was dissolved in THF (100 mL), to which 1% NaOH was then added. After stirring for 5 h at RT, the reaction mixture was extracted with ethyl acetate. The organic layer was washed with water and brine, dried over sodium sulfate and solvent was evaporated to provide the sub-title compound as a pale yellow solid. Yield: 8 g.
Workup
- additionwas then added
- extractionthe reaction mixture was extracted with ethyl acetate
- washThe organic layer was washed with water and brine
- dry with materialdried over sodium sulfate and solvent
- customwas evaporated
Sources & evidence
- ORD record
- ord-e04994d0e22040cdb6fb2c903fb41bd7
- Source dataset
- uspto-grants-2010_01
- Patent number
- US07648985B2
Reaction notes
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