Sodium Hydroxide → 5-(Pyridin-4-yl)-2,3-dihydro-1H-indole

HRID 1510227Notes

Reaction equation

HRID 1510227 reaction equation
C([N:4]1[C:12]2[C:7](=[CH:8][C:9]([C:13]3[CH:18]=[CH:17][N:16]=[CH:15][CH:14]=3)=[CH:10][CH:11]=2)[CH2:6][CH2:5]1)(=O)C.[OH-].[Na+]>C(O)C>[N:16]1[CH:17]=[CH:18][C:13]([C:9]2[CH:8]=[C:7]3[C:12](=[CH:11][CH:10]=2)[NH:4][CH2:5][CH2:6]3)=[CH:14][CH:15]=1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 132766931-Acetyl-5-(4-pyridinyl)indoline

Product 1

HCID 132766965-(Pyridin-4-yl)-2,3-dihydro-1H-indoleYield 40.8%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a suspension of 1-acetyl-5-(4-pyridinyl)indoline (715 mg) in ethanol (20 mL) was added 1N sodium hydroxide aqueous solution (1.8 mL) and the mixture was refluxed for 16 hours. The mixture was extracted with ethyl acetate and the separated organic layer was washed with brine, dried over magnesium sulfate, and evaporated in vacuo. The residue was purified by column chromatography on silica gel eluting with ethyl acetate to give 5-(4-pyridinyl)indoline (240 mg) as an yellow powder.

Workup

  1. temperaturethe mixture was refluxed for 16 hours
  2. extractionThe mixture was extracted with ethyl acetate
  3. washthe separated organic layer was washed with brine
  4. dry with materialdried over magnesium sulfate
  5. customevaporated in vacuo
  6. customThe residue was purified by column chromatography on silica gel eluting with ethyl acetate

Sources & evidence

ORD record
ord-c58ee90c8d83455181e3d897e5b4848d
Source dataset
uspto-grants-2012_07
Patent number
US08211919B2

Reaction notes

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