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

HRID 1964354Notes

Reaction equation

HRID 1964354 reaction equation
[CH2:1]([C:3]1[CH:4]=[C:5]2[C:9](=[CH:10][CH:11]=1)[N:8](S(C1C=CC=CC=1)(=O)=O)[CH2:7][CH2:6]2)[CH3:2].[OH-].[Na+]>Br>[CH2:1]([C:3]1[CH:4]=[C:5]2[C:9](=[CH:10][CH:11]=1)[NH:8][CH2:7][CH2:6]2)[CH3:2]

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 5-ethyl-1-(phenylsulfonyl)indoline (15 g, 0.050 mol) in HBr (48%, 162 mL) was heated at reflux for 6 h. The mixture was basified with sat. NaOH to pH 9 and then it was extracted with ethyl acetate. The organic layer was washed with brine, dried over Na2SO4, and concentrated under reduced pressure. The residue was purified by silica column to give 5-ethylindoline (2.5 g, 32%).

Workup

  1. temperaturewas heated
  2. temperatureat reflux for 6 h
  3. extractionit was extracted 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 silica column

Sources & evidence

ORD record
ord-2ebf8f320963452eb17f52ab6b2c6183
Source dataset
uspto-grants-2013_04
Patent number
US08415387B2

Reaction notes

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