1-(4-Nitrophenyl)propan-2-one → 4-Aminophenylacetone

HRID 1508844

Reaktionsgleichung

Reaktionsgleichung von HRID 1508844
[N+:1]([C:4]1[CH:9]=[CH:8][C:7]([CH2:10][C:11](=[O:13])[CH3:12])=[CH:6][CH:5]=1)([O-])=O>C(O)C.[Pd]>[NH2:1][C:4]1[CH:5]=[CH:6][C:7]([CH2:10][C:11](=[O:13])[CH3:12])=[CH:8][CH:9]=1

Komponenten

4

Edukt 1

HCID 2193671-(4-Nitrophenyl)propan-2-one

Produkt 1

HCID 117883794-AminophenylacetoneAusbeute 51,7 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 23938PalladiumKatalysatorHCID 702EthanolLösungsmittel

Versuchsvorschrift

To a solution of 1-(4-nitrophenyl)propan-2-one (0.650 g, 3.63 mmol) in ethanol (20 mL) was added 10% palladium on carbon (0.060 g) and the mixture stirred at rt under 1 atm of H2 for 1 h. After this time, the mixture was filtered over celite, concentrated, and the residue was purified by column chromatography (silica, hexanes/ethyl acetate) to afford the title compound (0.280 g, 51%) as an orange oil. MW=149.19. 1H NMR (CDCl3, 500 MHz) δ 7.00-6.96 (m, 2H), 6.68-6.63 (m, 2H), 3.63 (s, 2H), 3.56 (s, 2H), 2.11 (s, 3H); APCI MS m/z 150 [M+H]+.

Aufarbeitung

  1. filtrationAfter this time, the mixture was filtered over celite,
  2. concentrationconcentrated
  3. customthe residue was purified by column chromatography (silica, hexanes/ethyl acetate)

Quellen und Nachweise

ORD-Eintrag
ord-3b1bf0cbb0e64a1ba9ad2c7ac658cbe6
Quelldatensatz
uspto-grants-2015_12
Patentnummer
US09221843B2

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