4-Nitroquinoline 1-Oxide → 4-Aminoquinoline

HRID 1070463

Reaktionsgleichung

Reaktionsgleichung von HRID 1070463
[N+:1]([C:4]1[C:13]2[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=2)[N+:7]([O-])=[CH:6][CH:5]=1)([O-])=O>C(O)(=O)C.[Fe]>[NH2:1][C:4]1[C:13]2[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=2)[N:7]=[CH:6][CH:5]=1

Komponenten

4

Edukt 1

HCID 59554-Nitroquinoline 1-Oxide

Produkt 1

HCID 684764-AminoquinolineAusbeute 79,3 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 23925IronKatalysatorHCID 176Acetic AcidLösungsmittel

Reaktionsbedingungen

Temperatur
110 °C

Versuchsvorschrift

A suspension of 4-nitroquinoline N-oxide (10 g, 52.5 mmol) and metal iron (26.4 g, 0.47 mol) in acetic acid (500 ml) was stirred under heating at 110° C. for 3 hr. The reaction mixture was filtered and the filtrate was concentrated under reduced pressure. To the residue was added an aqueous sodium hydroxide solution to make the solution alkaline, which was followed by extraction with chloroform (50 ml×6). The organic layer was washed with water and saturated brine, dried over sodium sulfate and concentrated under reduced pressure to give 4-aminoquinoline (6.0 g, 79%, brown crystals).

Aufarbeitung

  1. filtrationThe reaction mixture was filtered
  2. concentrationthe filtrate was concentrated under reduced pressure
  3. additionTo the residue was added an aqueous sodium hydroxide solution
  4. extractionwas followed by extraction with chloroform (50 ml×6)
  5. washThe organic layer was washed with water and saturated brine
  6. dry with materialdried over sodium sulfate
  7. concentrationconcentrated under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-18e3e12d9263465fb139ad46caaeadec
Quelldatensatz
uspto-grants-2005_06
Patentnummer
US06903094B2

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