HCID 22132653, compound → HCID 22132721, compound

HRID 1857144Notes

Reaction equation

HRID 1857144 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][C:12]=1[O:13][CH3:14])[N:9]=[CH:8][CH:7]=[C:6]2[O:15][C:16]1[CH:21]=[CH:20][C:19]([NH:22][C:23]([C:25]2[CH:30]=[CH:29][C:28]([N+:31]([O-])=O)=[CH:27][CH:26]=2)=[O:24])=[CH:18][CH:17]=1>CN(C)C=O.C(OCC)(=O)C.[C].[Pd]>[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][C:12]=1[O:13][CH3:14])[N:9]=[CH:8][CH:7]=[C:6]2[O:15][C:16]1[CH:17]=[CH:18][C:19]([NH:22][C:23]([C:25]2[CH:30]=[CH:29][C:28]([NH2:31])=[CH:27][CH:26]=2)=[O:24])=[CH:20][CH:21]=1

Participants

4

Reactant 1

HCID 22132653HCID 22132653, compound

Product 1

HCID 22132721HCID 22132721, compoundYield 91.1%

Reagents, catalysts & solvents 2

HCID 178418390HCID 178418390, compoundCatalystHCID 22989253N,N-dimethylformamide ethyl acetateSolvent

Procedure

{4-[(6,7-Dimethoxy-4-quinolinyl)oxy]phenyl}-(4-nitrophenyl)carboxamide (100 mg) was dissolved in N,N-dimethylformamide/ethyl acetate (9 ml/5 ml), 10% palladium-carbon (69 mg) was added, and the admixture was stirred at room temperature under hydrogen for 22 hours. The reaction mixture was filtered using Celite. The filtrate was then distilled under reduced pressure to remove the solvents, and the resultant residue was purified by column chromatography on silica gel eluting chloroform/acetone to obtain 85 mg of the title compound (yield: 91%).

Workup

  1. filtrationThe reaction mixture was filtered
  2. distillationThe filtrate was then distilled under reduced pressure
  3. customto remove the solvents
  4. customthe resultant residue was purified by column chromatography on silica gel
  5. washeluting chloroform/acetone

Sources & evidence

ORD record
ord-23aa3712aa0e4c749200ac21f4a62c0f
Source dataset
uspto-grants-2000_11
Patent number
US06143764

Reaction notes

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