Sodium Hydroxide → 5-ethyl-2,3-dihydro-1H-indole

HRID 1529645Notes

Reaction equation

HRID 1529645 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

HCID 14798Sodium HydroxideHCID 141129525-Ethyl-1-(phenylsulfonyl)indoline

Product 1

HCID 167881195-ethyl-2,3-dihydro-1H-indoleYield 34%

Reagents, catalysts & solvents 1

HCID 260Hydrogen BromideSolvent

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

  1. temperaturewas heated
  2. temperatureat reflux for 6 h
  3. extractionextracted with ethyl acetate
  4. washThe organic layer was washed with brine
  5. dry with materialdried over Na2SO4
  6. concentrationconcentrated under reduced pressure
  7. customThe residue was purified by column chromatography on silica gel

Sources & evidence

ORD record
ord-4b81d822a19944109d24e57585f7c174
Source dataset
uspto-grants-2015_07
Patent number
US09090619B2

Reaction notes

Loading…