1-(2-Methoxyethoxy)-4-nitrobenzene → 4-(2-Methoxyethoxy)aniline

HRID 1621687Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1621687
[CH3:1][O:2][CH2:3][CH2:4][O:5][C:6]1[CH:11]=[CH:10][C:9]([N+:12]([O-])=O)=[CH:8][CH:7]=1>CCO.[Pd]>[CH3:1][O:2][CH2:3][CH2:4][O:5][C:6]1[CH:11]=[CH:10][C:9]([NH2:12])=[CH:8][CH:7]=1

Komponenten

4

Edukt 1

HCID 5478091-(2-Methoxyethoxy)-4-nitrobenzene

Produkt 1

HCID 38798854-(2-Methoxyethoxy)anilineAusbeute 89,3 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 23938PalladiumKatalysatorHCID 702EthanolLösungsmittel

Versuchsvorschrift

A mixture of 1-(2-methoxyethoxy)-4-nitrobenzene (0.724 g, 3.67 mmol) and 10% Pd/C (Aldrich) (0.201 g, 1.89 mmol) in EtOH (10 mL) was evacuated under vacuum and refilled with hydrogen (4 times). The mixture was hydrogenated under balloon pressure at rt for 1.5 h. The reaction mixture was filtered through a pad of Celite® (diatomaceous earth) (eluent:EtOH) and concentrated. The crude product was purified by silica gel chromatography (25 g, eluent: EtOAc in hexanes 0%-60%) to give 4-(2-methoxyethoxy)aniline (0.548 g, 89% yield) as a clear oil. 1H NMR (400 MHz, CDCl3) δ 6.73-6.82 (m, 2H); 6.58-6.68 (m, 2H); 4.01-4.08 (m, 2H); 3.67-3.76 (m, 2H); 3.29-3.52 (m, 5H). m/z (ESI, +ve ion) 168.1 (M+H)+.

Aufarbeitung

  1. customwas evacuated under vacuum
  2. additionrefilled with hydrogen (4 times)
  3. filtrationThe reaction mixture was filtered through a pad of Celite® (diatomaceous earth) (eluent:EtOH)
  4. concentrationconcentrated
  5. customThe crude product was purified by silica gel chromatography (25 g, eluent: EtOAc in hexanes 0%-60%)

Quellen und Nachweise

ORD-Eintrag
ord-776585c0595d4c42bde9d028923160e3
Quelldatensatz
uspto-grants-2014_07
Patentnummer
US08772480B2

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