4-Hydroxy-8-nitroquinoline-3-carboxylic acid → 8-Amino-4-hydroxyquinoline-3-carboxylic acid

HRID 1995337

Reaktionsgleichung

Reaktionsgleichung von HRID 1995337
[N+:1]([C:4]1[CH:5]=[CH:6][CH:7]=[C:8]2[C:13]=1[NH:12][CH:11]=[C:10]([C:14]([OH:16])=[O:15])[C:9]2=[O:17])([O-])=O.[H][H]>CN(C)C=O.[Ni]>[NH2:1][C:4]1[CH:5]=[CH:6][CH:7]=[C:8]2[C:13]=1[NH:12][CH:11]=[C:10]([C:14]([OH:16])=[O:15])[C:9]2=[O:17]

Komponenten

5

Edukt 2

HCID 2259064-Hydroxy-8-nitroquinoline-3-carboxylic acidHCID 178418361HCID 178418361, Verbindung

Produkt 1

HCID 128663498-Amino-4-hydroxyquinoline-3-carboxylic acidAusbeute 74,2 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 935NickelKatalysatorHCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

A solution of 15.0 g (64 mmol) of 1,4-dihydro-8-nitro-4-oxo-3-quinolinecarboxylic acid [J. Amer. Chem. Soc. 68, 1264 (1946)] in 300 ml of dimethylformamide is hydrogenated using 1 g of Raney nickel catalyst at 51 psi and 23° C. until the required amount of hydrogen uptake is obtained. The catalyst is filtered off and the filtrate is concentrated to 50 ml and ethanol is added. The solid is collected by filtration and washed with ethanol and ether to give 9.7 g of the title compound.

Aufarbeitung

  1. customat 51 psi and 23° C.
  2. customis obtained
  3. filtrationThe catalyst is filtered off
  4. concentrationthe filtrate is concentrated to 50 ml and ethanol
  5. additionis added
  6. filtrationThe solid is collected by filtration
  7. washwashed with ethanol and ether

Quellen und Nachweise

ORD-Eintrag
ord-ce9b252291124283b4806010140d3fe8
Quelldatensatz
uspto-grants-1983_09
Patentnummer
US04404201

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