Sodium Hydroxide → 5-ethyl-2,3-dihydro-1H-indole
Reaction equation
C1(S([N:10]2[C:18]3[C:13](=[CH:14][C:15]([CH2:19][CH3:20])=[CH:16][CH:17]=3)[CH2:12][CH2:11]2)(=O)=O)C=CC=CC=1.[OH-].[Na+]>Br>[CH2:19]([C:15]1[CH:14]=[C:13]2[C:18](=[CH:17][CH:16]=1)[NH:10][CH2:11][CH2:12]2)[CH3:20]Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Procedure
A mixture of 1-benzenesulfonyl-5-ethyl-2,3-dihydro-1H-indole (15 g, 0.05 mol) in HBr (48%, 162 mL) was heated at reflux for 6 h. The mixture was basified with sat. NaOH solution to pH 9 and extracted with ethyl acetate. The organic layer was washed with brine, dried over Na2SO4 and concentrated under reduced pressure. The residue was purified by column chromatography on silica gel to give 5-ethyl-2,3-dihydro-1H-indole (2.5 g, 32%).
Workup
- temperaturewas heated
- temperatureat reflux for 6 h
- extractionextracted with ethyl acetate
- washThe organic layer was washed with brine
- dry with materialdried over Na2SO4
- concentrationconcentrated under reduced pressure
- customThe residue was purified by column chromatography on silica gel
Sources & evidence
- ORD record
- ord-2a92c40e07ad45bfada1cd9663177e5f
- Source dataset
- uspto-grants-2014_09
- Patent number
- US08829204B2
Reaction notes
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