Dimethylformamide → 6-amino-N-[(4-chlorophenyl)methyl]-4-hydroxy-3-quinolinecarboxamide

HRID 2289915Notes

Reaction equation

HRID 2289915 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][NH:9][C:10]([C:12]2[CH:13]=[N:14][C:15]3[C:20]([C:21]=2[OH:22])=[CH:19][C:18]([N+:23]([O-])=O)=[CH:17][CH:16]=3)=[O:11])=[CH:4][CH:3]=1.CN(C)C=O.[H][H]>[Ni].O>[NH2:23][C:18]1[CH:19]=[C:20]2[C:15](=[CH:16][CH:17]=1)[N:14]=[CH:13][C:12]([C:10]([NH:9][CH2:8][C:5]1[CH:6]=[CH:7][C:2]([Cl:1])=[CH:3][CH:4]=1)=[O:11])=[C:21]2[OH:22]

Participants

6

Reactant 3

HCID 6228DimethylformamideHCID 178418361HCID 178418361, compoundHCID 178522883HCID 178522883, compound

Product 1

HCID 1785073346-amino-N-[(4-chlorophenyl)methyl]-4-hydroxy-3-quinolinecarboxamideYield 84.5%

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 962WaterSolvent

Procedure

N-[(4-chlorophenyl)methyl]-4-hydroxy-6-nitro-3-quinolinecarboxamide (500 mg) is suspended in 50 mL of freshly degassed dimethylformamide and treated with 0.5 mL of 50% Raney nickel in water (Aldrich). The mixture is agitated under 45 psi hydrogen pressure for 24 h, and then it is filtered through celite. The solvent is removed by evaporation at reduced pressure and the residue is suspended in 5 mL of absolute ethanol and it is collected by filtration. After drying at 0.1 torr/100 ° C./1.5 h, the product is obtained as 387 mg of a pale yellow powder.

Workup

  1. filtrationit is filtered through celite
  2. customThe solvent is removed by evaporation at reduced pressure
  3. filtrationit is collected by filtration
  4. customAfter drying at 0.1 torr/100 ° C./1.5 h

Sources & evidence

ORD record
ord-29cca363d5bb404f9c8c50532aac403f
Source dataset
uspto-grants-2000_07
Patent number
US06093732

Reaction notes

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