1-(2,3-Dihydro-1H-indol-1-yl)ethan-1-one → HCID 23003913, compound

HRID 396730Notes

Reaction equation

HRID 396730 reaction equation
[C:1](Cl)(=[O:6])[CH2:2][CH2:3][CH2:4][CH3:5].[Cl-].[Al+3].[Cl-].[Cl-].[C:12]([N:15]1[C:23]2[C:18](=[CH:19][CH:20]=[CH:21][CH:22]=2)[CH2:17][CH2:16]1)(=[O:14])[CH3:13]>ClCCCl>[C:12]([N:15]1[C:23]2[C:18](=[CH:19][C:20]([C:1](=[O:6])[CH2:2][CH2:3][CH2:4][CH3:5])=[CH:21][CH:22]=2)[CH2:17][CH2:16]1)(=[O:14])[CH3:13]

Participants

5

Reactant 3

HCID 276731-(2,3-Dihydro-1H-indol-1-yl)ethan-1-oneHCID 61186Valeryl chlorideHCID 6451240Aluminum(III) Chloride

Product 1

HCID 23003913HCID 23003913, compoundYield 67.7%

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent

Procedure

Pentanoyl chloride (10.8 g) was added dropwise to a mixture of anhydrous aluminium chloride (28.2 g) and 1-acetyl-2,3-dihydro-1H-indole (10 g) in 1,2-dichloroethane (100 mL) with mechanical stirring. The mixture was stirred at reflux for 16 hours, then cooled, then poured into ice-water. The mixture was extracted with dichloromethane. The extracts were washed with 1M aqueous sodium hydroxide, then dried over magnesium sulphate, then evaporated to give the title compound (10.3 g) as a dark gum.

Workup

  1. temperatureat reflux for 16 hours
  2. temperaturecooled
  3. extractionThe mixture was extracted with dichloromethane
  4. washThe extracts were washed with 1M aqueous sodium hydroxide
  5. dry with materialdried over magnesium sulphate
  6. customevaporated

Sources & evidence

ORD record
ord-983e5b93406241a581f3a7c51cb9d1a9
Source dataset
uspto-grants-2003_08
Patent number
US06608084B1

Reaction notes

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