2-Nitro-6-n-propylphenol → 2-Amino-6-propylphenol

HRID 1385410Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1385410
[N+:1]([C:4]1[CH:9]=[CH:8][CH:7]=[C:6]([CH2:10][CH2:11][CH3:12])[C:5]=1[OH:13])([O-])=O>CO.[Pd]>[NH2:1][C:4]1[CH:9]=[CH:8][CH:7]=[C:6]([CH2:10][CH2:11][CH3:12])[C:5]=1[OH:13]

Komponenten

4

Edukt 1

HCID 150363142-Nitro-6-n-propylphenol

Produkt 1

HCID 4133782-Amino-6-propylphenolAusbeute 90,2 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 23938PalladiumKatalysatorHCID 887MethanolLösungsmittel

Versuchsvorschrift

To a solution of 2-nitro-6-n-propylphenol (2 g, 11.0 mmol) in methanol (100 mL) was added 10% Pd/C (200 mg). The mixture was flushed with argon, then hydrogen was bubbled through the solution for 10 min. and a hydrogen atmosphere was maintained at balloon pressure overnight. The mixture was filtered through celite and the celite was washed with methanol. The solvent was evaporated and chromatography of the resulting solid on silica gel (5%MeOH/CH2CH2) gave the desired product (1.50 g, 80.2%). 1H NMR (CD3OD): d 6.65 (m, 2H), 6.55 (t, 1H), 2.58 (t, 2H), 1.61 (m, 2H), 0.96 (t, 3H).

Aufarbeitung

  1. customThe mixture was flushed with argon
  2. customhydrogen was bubbled through the solution for 10 min.
  3. temperaturea hydrogen atmosphere was maintained at balloon pressure overnight
  4. filtrationThe mixture was filtered through celite
  5. washthe celite was washed with methanol
  6. customThe solvent was evaporated

Quellen und Nachweise

ORD-Eintrag
ord-3628ccdb79be40aaa93ec5ef8edb8f5e
Quelldatensatz
uspto-grants-2001_07
Patentnummer
US06262113B1

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