Sodium Hydroxide → 2-ethyl-1H-indole

HRID 1640262Notes

Reaction equation

HRID 1640262 reaction equation
C1(S([N:10]2[C:18]3[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=3)[CH:12]=[C:11]2[CH2:19][CH3:20])(=O)=O)C=CC=CC=1.[OH-].[Na+]>CCO>[CH2:19]([C:11]1[NH:10][C:18]2[C:13]([CH:12]=1)=[CH:14][CH:15]=[CH:16][CH:17]=2)[CH3:20]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 100167951H-Indole, 2-ethyl-1-(phenylsulfonyl)-

Product 1

HCID 38016182-ethyl-1H-indole

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

1.2 g (4.2 mmol) 1-benzenesulphonyl-2-ethyl-1H-indole in 10 mL EtOH were mixed with 5 mL of a (20 mmol) 4 N aqueous sodium hydroxide solution and refluxed for 8 h. Then the solvent was eliminated using the rotary evaporator and the residue was diluted with ice water. After acidifying with semi-concentrated aqueous hydrochloric acid the grease precipitated was extracted with ethyl acetate. The organic phase was dried on sodium sulphate, filtered off, evaporated down and dried.

Workup

  1. temperaturerefluxed for 8 h
  2. customthe rotary evaporator
  3. additionthe residue was diluted with ice water
  4. customprecipitated
  5. extractionwas extracted with ethyl acetate
  6. customThe organic phase was dried on sodium sulphate
  7. filtrationfiltered off
  8. customevaporated down
  9. customdried

Sources & evidence

ORD record
ord-094b616f5d2c4671b06709475f699832
Source dataset
uspto-grants-2012_02
Patent number
US08110575B2

Reaction notes

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