Triethylamine → 5-Aminoindole

HRID 1419166Notes

Reaction equation

HRID 1419166 reaction equation
CC1[N:3]([C:8]2[CH:9]=[C:10]3[C:14](=[CH:15][CH:16]=2)[NH:13][CH:12]=[CH:11]3)C(C)=CC=1.Cl.NO.C(N(CC)CC)C.[OH-].[Na+]>CC(O)C.O>[NH2:3][C:8]1[CH:9]=[C:10]2[C:14](=[CH:15][CH:16]=1)[NH:13][CH:12]=[CH:11]2

Participants

7

Reactant 4

HCID 8471TriethylamineHCID 14798Sodium HydroxideHCID 443297Hydroxyamine hydrochlorideHCID 100818535-(2,5-Dimethyl-1H-pyrrol-1-yl)-1H-indole

Product 1

HCID 788675-Aminoindole

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 3776IsopropanolSolvent

Procedure

A mixture of the 5-(2,5-dimethyl-1H-pyrrol-1-yl)-1H-indole (10.00 mmol), hydroxylamine hydrochloride (6.95 g, 100 mmol, 10 eq), and triethylamine (6.97 mL, 50.0 mmol, 5 eq) in 2-propanol (35 mL) and water (5 mL) was heated at reflux under nitrogen for a time depending on the substrate. The resulting reaction mixture was cooled, solid sodium hydroxide (4.00 g, 100 mmol, 10 eq) was added, and the resulting reaction mixture was stirred at room temperature under nitrogen for 24 hours. The reaction mixture was then filtered through Celite®, and the filtrate was evaporated under reduced pressure. The residue was column chromatographed using silica gel (approximately 100 g) and eluting with an appropriate solvent system to afford the appropriate 5amino-1H-indole.

Workup

  1. temperaturewas heated
  2. temperatureat reflux under nitrogen for a time
  3. customThe resulting reaction mixture
  4. temperaturewas cooled
  5. customthe resulting reaction mixture
  6. filtrationThe reaction mixture was then filtered through Celite®
  7. customthe filtrate was evaporated under reduced pressure
  8. customchromatographed
  9. washeluting with an appropriate solvent system

Sources & evidence

ORD record
ord-f47359dd4050490e9f6f265bbea4c541
Source dataset
uspto-grants-1999_03
Patent number
US05886008

Reaction notes

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