Ammonium formate → Ethyl 5-amino-1-ethyl-1H-indole-2-carboxylate

HRID 489988Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 489988
[CH2:1]([O:3][C:4]([C:6]1[N:7]([CH2:18][CH3:19])[C:8]2[C:13]([CH:14]=1)=[CH:12][C:11]([N+:15]([O-])=O)=[CH:10][CH:9]=2)=[O:5])[CH3:2].C([O-])=O.[NH4+]>CCO.C(O)CC.[OH-].[Pd+2].[OH-]>[CH2:1]([O:3][C:4]([C:6]1[N:7]([CH2:18][CH3:19])[C:8]2[C:13]([CH:14]=1)=[CH:12][C:11]([NH2:15])=[CH:10][CH:9]=2)=[O:5])[CH3:2]

Komponenten

5

Edukt 2

HCID 2723923Ammonium formateHCID 12148796ethyl 1-ethyl-5-nitro-1H-indole-2-carboxylate

Produkt 1

HCID 12148797Ethyl 5-amino-1-ethyl-1H-indole-2-carboxylateAusbeute 90,2 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 9942167Palladium hydroxideKatalysatorHCID 9793718EtOH n-PrOHLösungsmittel

Versuchsvorschrift

The 1-ethyl-5-nitro-1H-indole-2-carboxylic acid ethyl ester (5 g, 19.1 mmol) of step (a) was dissolved in EtOH/n-PrOH (100 mL, 1/1). Palladium hydroxide (1.14 g) and ammonium formate (3.92 g, 62.2 mmol) were added to the above solution. The mixture was heated to reflux for 2 hours. The reaction mixture was cooled to room temperature and the catalyst was filtered off through Celite. The solvent was removed under reduced pressure. The crude product was dissolved in dichloromethane (300 mL) and washed with NaHCO3 (150 ml×2). The organic layer was collected, dried (Na2SO4) and evaporated. The crude product was purified by chromatography to furnish the desired product (4 g, 90%).

Aufarbeitung

  1. temperatureThe mixture was heated
  2. temperatureto reflux for 2 hours
  3. filtrationthe catalyst was filtered off through Celite
  4. customThe solvent was removed under reduced pressure
  5. dissolutionThe crude product was dissolved in dichloromethane (300 mL)
  6. washwashed with NaHCO3 (150 ml×2)
  7. customThe organic layer was collected
  8. dry with materialdried (Na2SO4)
  9. customevaporated
  10. customThe crude product was purified by chromatography

Quellen und Nachweise

ORD-Eintrag
ord-860473b917d3440c8123ddd457c26dfd
Quelldatensatz
uspto-grants-2005_12
Patentnummer
US06979692B2

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