Quinoline, 6,7-dimethoxy-4-(4-nitrophenoxy)- → 4-[(6,7-Dimethoxyquinolin-4-yl)oxy]aniline

HRID 1857135Notes

Reaction equation

HRID 1857135 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]([N+:22]([O-])=O)=[CH:18][CH:17]=1>CN(C)C=O.C(OCC)(=O)C.[OH-].[Pd+2].[OH-].[C]>[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]([NH2:22])=[CH:20][CH:21]=1

Participants

4

Reactant 1

HCID 22132806Quinoline, 6,7-dimethoxy-4-(4-nitrophenoxy)-

Product 1

HCID 115945434-[(6,7-Dimethoxyquinolin-4-yl)oxy]anilineYield 88%

Reagents, catalysts & solvents 2

HCID 178502593HCID 178502593, compoundCatalystHCID 22989253N,N-dimethylformamide ethyl acetateSolvent

Procedure

6,7-Dimethoxy-4-(4-nitrophenoxy)quinoline (1.00 g) was dissolved in N,N-dimethylformamide/ethyl acetate (30 ml/15 ml), 10% palladium hydroxide-carbon (69 mg) was added, and the admixture was stirred at room temperature under hydrogen for 17 hours. The reaction mixture was filtered using Celite. The filtrate was washed with brine and then dried with anhydrous sodium sulfate. The solvent was removed by reduced-pressure distillation to obtain 799 mg of the title compound (yield: 88%).

Workup

  1. filtrationThe reaction mixture was filtered
  2. washThe filtrate was washed with brine
  3. dry with materialdried with anhydrous sodium sulfate
  4. customThe solvent was removed by reduced-pressure distillation

Sources & evidence

ORD record
ord-a2bb4926df6142fcae3b0cdeee4e0187
Source dataset
uspto-grants-2000_11
Patent number
US06143764

Reaction notes

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