1-(2,2,2-Trifluoroacetyl)indoline-5-carbonitrile → 2,3-Dihydro-1H-indole-5-carbonitrile

HRID 1992339Notes

Reaction equation

HRID 1992339 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]1

Participants

4

Reactant 1

HCID 866259911-(2,2,2-Trifluoroacetyl)indoline-5-carbonitrile

Product 1

HCID 219076392,3-Dihydro-1H-indole-5-carbonitrile

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 14798Sodium HydroxideSolvent

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

  1. additionwas then added
  2. extractionthe reaction mixture was extracted with ethyl acetate
  3. washThe organic layer was washed with water and brine
  4. dry with materialdried over sodium sulfate and solvent
  5. customwas evaporated

Sources & evidence

ORD record
ord-e04994d0e22040cdb6fb2c903fb41bd7
Source dataset
uspto-grants-2010_01
Patent number
US07648985B2

Reaction notes

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