(3-Nitro-5-(trifluoromethyl)phenyl)methanol → (3-Amino-5-(trifluoromethyl)phenyl)methanol

HRID 391377

Reaktionsgleichung

Reaktionsgleichung von HRID 391377
[N+:1]([C:4]1[CH:5]=[C:6]([CH2:14][OH:15])[CH:7]=[C:8]([C:10]([F:13])([F:12])[F:11])[CH:9]=1)([O-])=O>CO.[Pd]>[NH2:1][C:4]1[CH:5]=[C:6]([CH2:14][OH:15])[CH:7]=[C:8]([C:10]([F:11])([F:12])[F:13])[CH:9]=1

Komponenten

4

Edukt 1

HCID 18621888(3-Nitro-5-(trifluoromethyl)phenyl)methanol

Produkt 1

HCID 53414333(3-Amino-5-(trifluoromethyl)phenyl)methanol

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 23938PalladiumKatalysatorHCID 887MethanolLösungsmittel

Versuchsvorschrift

(3-Nitro-5-(trifluoromethyl)phenyl)methanol (2.6 g, 11.6 mmol) in methanol (30 mL) was flushed with nitrogen, and treated with palladium (10% on charcoal, 260 mg). The flask was flushed with hydrogen and allowed to stir under an atmosphere of hydrogen overnight. The reaction was flushed with nitrogen, filtered through celite, and concentrated. Column chromatography on silica gel (50% ethyl acetate/hexanes) afforded 1.9 g (85%). 1H-NMR (CDCl3, 500 MHz) δ 6.95 (s, 1H), 6.80 (s, 1H), 6.79 (s, 1H), 4.61 (s, 2H). Mass spec.: 192.15 (MH)+.

Aufarbeitung

  1. customThe flask was flushed with hydrogen
  2. customThe reaction was flushed with nitrogen
  3. filtrationfiltered through celite
  4. concentrationconcentrated
  5. customColumn chromatography on silica gel (50% ethyl acetate/hexanes) afforded 1.9 g (85%)

Quellen und Nachweise

ORD-Eintrag
ord-c5431651436b4c4ba551a8949bf0c2a6
Quelldatensatz
uspto-grants-2013_02
Patentnummer
US08383821B2

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