Sodium Hydroxide → 4-[2-(Dipropylamino)ethyl]indol-2-one

HRID 1766627Notes

Reaction equation

HRID 1766627 reaction equation
[Br-].[Br-].[Br-].[NH+]1C=CC=CC=1.[NH+]1C=CC=CC=1.[NH+]1C=CC=CC=1.[CH2:22]([N:25]([CH2:37][CH2:38][CH3:39])[CH2:26][CH2:27][C:28]1[CH:36]=[CH:35][CH:34]=[C:33]2[C:29]=1[CH:30]=[CH:31][NH:32]2)[CH2:23][CH3:24].[OH-:40].[Na+]>C(O)(=O)C.O>[CH2:37]([N:25]([CH2:22][CH2:23][CH3:24])[CH2:26][CH2:27][C:28]1[C:29]2[C:33]([CH:34]=[CH:35][CH:36]=1)=[N:32][C:31](=[O:40])[CH:30]=2)[CH2:38][CH3:39]

Participants

6

Reactant 3

HCID 14798Sodium HydroxideHCID 30860544-(2-di-N-propylaminoethyl)indoleHCID 21124087Pyridiniumtribromide

Product 1

HCID 211117034-[2-(Dipropylamino)ethyl]indol-2-oneYield 81%

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolvent2×HCID 962WaterSolvent

Conditions

Temperature
50 °C

Procedure

A solution of pyridinium tribromide 90% (8.72 g, 24.5 mmol) in acetic acid 50% (50 mL) was added to a solution of 4-[2-(dipropylamino)ethyl]indol (IV) (5 g, 20.5 mmol) in acetic acid 50% (100 mL) and was stirred at 50° C. for 3 h. When the resultant mixture reached room temperature, it was stirred at this temperature for 16 h. The reaction mixture was concentrated to obtain an aqueous residue, which was diluted with water (100 mL), basified with an aqueous solution of NaOH 10% and extracted with AcOEt. The organic layer was dried, filtered and concentrated to obtain 4.3 g (81%) of 4-[2-(dipropylamino)ethyl]indol-2-one (I).

Workup

  1. customreached room temperature
  2. stirringit was stirred at this temperature for 16 h
  3. concentrationThe reaction mixture was concentrated
  4. customto obtain an aqueous residue, which
  5. extractionextracted with AcOEt
  6. customThe organic layer was dried
  7. filtrationfiltered
  8. concentrationconcentrated

Sources & evidence

ORD record
ord-1147c6840cf9490fb4cdbad9a84c5ba5
Source dataset
uspto-grants-2007_06
Patent number
US07230118B2

Reaction notes

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