N-methyl-3-(4-nitrophenoxy)benzamide → 3-(4-Aminophenoxy)-N-methylbenzamide

HRID 598448

Reaktionsgleichung

Reaktionsgleichung von HRID 598448
[CH3:1][NH:2][C:3]([C:5]1[CH:6]=[C:7]([CH:18]=[CH:19][CH:20]=1)[O:8][C:9]1[CH:14]=[CH:13][C:12]([N+:15]([O-])=O)=[CH:11][CH:10]=1)=[O:4]>CCOC(C)=O.[Pd]>[CH3:1][NH:2][C:3]([C:5]1[CH:6]=[C:7]([CH:18]=[CH:19][CH:20]=1)[O:8][C:9]1[CH:14]=[CH:13][C:12]([NH2:15])=[CH:11][CH:10]=1)=[O:4]

Komponenten

4

Edukt 1

HCID 23614569N-methyl-3-(4-nitrophenoxy)benzamide

Produkt 1

HCID 236145703-(4-Aminophenoxy)-N-methylbenzamideAusbeute 56,4 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 23938PalladiumKatalysatorHCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

A slurry of 4-(3-(N-methylcarbamoyl)phenoxy)-1-nitrobenzene (1.89 g, 6.95 mmol) and 5% Pd/C (0.24 g) in EtOAc (20 mL) was stirred under an H2 atm (balloon) overnight. The resulting mixture was filtered through a pad of Celite® and concentrated under reduced pressure. The residue was purified by column chromatography (5% MeOH/95% CH2Cl2). The resulting oil solidified under vacuum overnight to give 4-(3-(N-methylcarbamoyl)phenoxy)aniline as a yellow solid (0.95 g, 56%).

Aufarbeitung

  1. filtrationThe resulting mixture was filtered through a pad of Celite®
  2. concentrationconcentrated under reduced pressure
  3. customThe residue was purified by column chromatography (5% MeOH/95% CH2Cl2)
  4. customsolidified under vacuum overnight

Quellen und Nachweise

ORD-Eintrag
ord-0d096a36eb0c44f6b7fce3e800d192fd
Quelldatensatz
uspto-grants-2011_03
Patentnummer
US07897623B2

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