N-(2-tert-butyl-5-nitrophenyl)-2-(dimethylamino)acetamide → Ammonium Hydroxide

HRID 1815163Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1815163
[C:1]([C:5]1[CH:10]=[CH:9][C:8]([N+:11]([O-])=[O:12])=[CH:7][C:6]=1[NH:14][C:15](=[O:20])[CH2:16][N:17]([CH3:19])[CH3:18])([CH3:4])([CH3:3])[CH3:2]>CCO.O1CCOCC1>[NH4+:11].[OH-:12].[NH2:11][C:8]1[CH:9]=[CH:10][C:5]([C:1]([CH3:4])([CH3:3])[CH3:2])=[C:6]([NH:14][C:15](=[O:20])[CH2:16][N:17]([CH3:18])[CH3:19])[CH:7]=1

Komponenten

5

Edukt 1

HCID 21961377N-(2-tert-butyl-5-nitrophenyl)-2-(dimethylamino)acetamide

Produkt 2

HCID 14923Ammonium HydroxideHCID 21961467HCID 21961467, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 702EthanolLösungsmittelHCID 312751,4-DioxaneLösungsmittel

Versuchsvorschrift

N-(2-tert-Butyl-5-nitro-phenyl)-2-dimethylamino-acetamide (25.8 g, 92 mmol) was dissolved in EtOH (1.4 L) and 1,4-dioxane (200 mL). The solution was degassed under vacuum with stirring. 10% Pd/C (2.5 g) was added (as a slurry in EtOH). The mixture was degassed again, then the reaction vessel was charged with H2 gas (balloon) and stirred overnight at RT. The reaction was filtered through Celite® with MeOH and the filtrate was concentrated under reduced pressure. The recovered material was eluted through a 36×7 cm column of silica gel with a 97.5:2.5:0.25 and 95:5:0.5 CH2Cl2:MeOH:NH4OH(aq) step gradient giving N-(5-amino-2-tert-butyl-phenyl)-2-dimethylamino-acetamide as a brown solid.

Aufarbeitung

  1. customThe solution was degassed under vacuum
  2. addition10% Pd/C (2.5 g) was added (as a slurry in EtOH)
  3. customThe mixture was degassed again
  4. additionthe reaction vessel was charged with H2 gas (balloon)
  5. stirringstirred overnight at RT
  6. filtrationThe reaction was filtered through Celite® with MeOH
  7. concentrationthe filtrate was concentrated under reduced pressure
  8. washThe recovered material was eluted through a 36×7 cm column of silica gel with a 97.5:2.5:0.25 and 95:5:0.5 CH2Cl2

Quellen und Nachweise

ORD-Eintrag
ord-6bd26cc8ad0a4f54ac0695aef9ad8fb9
Quelldatensatz
uspto-grants-2005_04
Patentnummer
US06878714B2

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