5-Nitro-1,2-dihydroquinolin-2-one → 5-Amino-1,2-dihydroquinolin-2-one

HRID 1035856

Reaktionsgleichung

Reaktionsgleichung von HRID 1035856
[N+:1]([C:4]1[CH:13]=[CH:12][CH:11]=[C:10]2[C:5]=1[CH:6]=[CH:7][C:8](=[O:14])[NH:9]2)([O-])=O.[H][H]>CC(O)=O.[Pd]>[NH2:1][C:4]1[CH:13]=[CH:12][CH:11]=[C:10]2[C:5]=1[CH:6]=[CH:7][C:8](=[O:14])[NH:9]2

Komponenten

5

Edukt 2

HCID 2437765-Nitro-1,2-dihydroquinolin-2-oneHCID 178418361HCID 178418361, Verbindung

Produkt 1

HCID 157190785-Amino-1,2-dihydroquinolin-2-oneAusbeute 97 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 23938PalladiumKatalysatorHCID 176Acetic AcidLösungsmittel

Versuchsvorschrift

A solution of 2.1 g (11 mmol) of 5-nitro-1H-quinolin-2-one (Chem. Pharm. Bull. 1981, 29, 651) in 40 ml of AcOH is hydrogenated with 210 mg of 10% Pd/C in the presence of hydrogen for 24 h with vigorous stirring. The catalyst is filtered off and the mixture is evaporated. The residue is subjected to flash chromatography over SiO2 with a gradient of pure CH2Cl2 to CH2Cl2-MeOH 99-1. After evaporation, 1.67 g (yield 97%) of yellow crystals are obtained. 1H NMR (DMSO): 11.38 (s, 1H), 8.08 (d, 1H, J=8 Hz), 7.10 (t, 1H, J=7.6 Hz), 6.44 (d, 1H, J=8 Hz), 6.33 (d, 1H, J=8 Hz), 6.26 (d, 1H, J=10 Hz), 5.85 (s, 2H).

Aufarbeitung

  1. filtrationThe catalyst is filtered off
  2. customthe mixture is evaporated

Quellen und Nachweise

ORD-Eintrag
ord-fda20f2d4bbb43c3b85e8f382069d939
Quelldatensatz
uspto-grants-2013_10
Patentnummer
US08546402B2

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