Ethyl Acetate → 2-(1H-Indol-4-yl)ethan-1-amine

HRID 1766625Notes

Reaction equation

HRID 1766625 reaction equation
[N+:1]([CH:4]=[CH:5][C:6]1[CH:14]=[CH:13][CH:12]=[C:11]2[C:7]=1[CH:8]=[CH:9][NH:10]2)([O-])=O.CC(C[AlH]CC(C)C)C.CCOC(C)=O.[OH-].[K+]>C1COCC1.O>[NH2:1][CH2:4][CH2:5][C:6]1[CH:14]=[CH:13][CH:12]=[C:11]2[C:7]=1[CH:8]=[CH:9][NH:10]2

Participants

7

Reactant 4

HCID 8857Ethyl AcetateHCID 14487Diisobutylaluminum hydrideHCID 14797Potassium HydroxideHCID 533951384-(2-Nitrovinyl)-1H-indole

Product 1

HCID 131009012-(1H-Indol-4-yl)ethan-1-amine

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

A solution of 4-(2-nitrovinyl)indole (II) (3 g, 15.9 mmol) in THF (10 ml) was added to a suspension of DIBAH (1M THF, 159 ml, 159 mmol) under an inert atmosphere and was stirred at room temperature for 30 min, then it was heated at 60° C. and stirred for 5 hours. The obtained mixture was cooled to 0° C., AcOEt, water and KOH 10% were added and the ontained product was filtered. The aqueous layer was extracted with AcOEt and the organic layer was dried and evaporated to obtain 4-[(2-amino)ethyl]indole (III).

Workup

  1. temperatureit was heated at 60° C.
  2. stirringstirred for 5 hours
  3. temperatureThe obtained mixture was cooled to 0° C.
  4. filtrationthe ontained product was filtered
  5. extractionThe aqueous layer was extracted with AcOEt
  6. customthe organic layer was dried
  7. customevaporated

Sources & evidence

ORD record
ord-4e4163b7db87439fb1af2999ce96e87d
Source dataset
uspto-grants-2007_06
Patent number
US07230118B2

Reaction notes

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