2-Hydroxy-6-nitroquinoline-3-carboxylic acid → 6-Amino-2-oxo-1,2-dihydroquinoline-3-carboxylic acid

HRID 850995Notes

Reaction equation

HRID 850995 reaction equation
[N+:1]([C:4]1[CH:5]=[C:6]2[C:11](=[CH:12][CH:13]=1)[NH:10][C:9](=[O:14])[C:8]([C:15]([OH:17])=[O:16])=[CH:7]2)([O-])=O.[H][H]>[Ni].CN(C)C=O>[NH2:1][C:4]1[CH:5]=[C:6]2[C:11](=[CH:12][CH:13]=1)[NH:10][C:9](=[O:14])[C:8]([C:15]([OH:17])=[O:16])=[CH:7]2

Participants

5

Reactant 2

HCID 131063292-Hydroxy-6-nitroquinoline-3-carboxylic acidHCID 178418361HCID 178418361, compound

Product 1

HCID 131063306-Amino-2-oxo-1,2-dihydroquinoline-3-carboxylic acid

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 6228DimethylformamideSolvent

Procedure

A solution of 3.63 g (14.9 mmol) of 1,2-dihydro-6-nitro-2-oxo-3-quinolinecarboxylic acid and 200 ml of dimethylformamide is hydrogenated using 1 g of Raney nickel catalyst at 52 psi and 23° until the required amount of hydrogen uptake is obtained. The catalyst is filtered off and the filtrate is evaporated to dryness. The residue is treated with ethanol and 3.0 g of the desired product is filtered.

Workup

  1. customat 52 psi and 23°
  2. customis obtained
  3. filtrationThe catalyst is filtered off
  4. customthe filtrate is evaporated to dryness
  5. additionThe residue is treated with ethanol and 3.0 g of the desired product
  6. filtrationis filtered

Sources & evidence

ORD record
ord-73a3bd3170bf43e8ba3e0e1af1410cc3
Source dataset
uspto-grants-1983_05
Patent number
US04382089

Reaction notes

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