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

HRID 1995337

Reaction equation

HRID 1995337 reaction equation
[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]

Participants

5

Reactant 2

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

Product 1

HCID 128663498-Amino-4-hydroxyquinoline-3-carboxylic acidYield 74.2%

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 6228DimethylformamideSolvent

Procedure

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.

Workup

  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

Sources & evidence

ORD record
ord-ce9b252291124283b4806010140d3fe8
Source dataset
uspto-grants-1983_09
Patent number
US04404201

Linked notes

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