Sodium Bicarbonate → N-{4-[(6,7-Dimethoxy-4-quinolinyl)oxy]phenyl}-4-biphenylcarboxamide

HRID 1857147Notes

Reaction equation

HRID 1857147 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]([NH2:22])=[CH:18][CH:17]=1.[C:23]1([C:32]2[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=2)[C:24](C(Cl)=O)=[CH:25][CH:26]=[CH:27][CH:28]=1.[C:38](=O)([O-])[OH:39].[Na+]>C(N(CC)CC)C.C(Cl)Cl>[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:38]([C:35]2[CH:34]=[CH:33][C:32]([C:23]3[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=3)=[CH:37][CH:36]=2)=[O:39])=[CH:20][CH:21]=1

Participants

5

Reactant 3

HCID 516892Sodium BicarbonateHCID 115945434-[(6,7-Dimethoxyquinolin-4-yl)oxy]anilineHCID 12563768[1,1'-Biphenyl]-2-carbonyl chloride

Product 1

HCID 22132658N-{4-[(6,7-Dimethoxy-4-quinolinyl)oxy]phenyl}-4-biphenylcarboxamideYield 10%

Reagents, catalysts & solvents 1

HCID 21882572Triethylamine methylene chlorideSolvent

Procedure

6,7-Dimethoxy-4-(4-aminophenoxy)quinoline (52 mg) was suspended in triethylamine/methylene chloride (3 ml/2 ml), commercially available biphenylcarbonyl chloride (80 mg) was added, and the admixture was stirred at room temperature for 25 hours. Aqueous sodium hydrogen carbonate was added to the reaction mixture, and the resulting admixture was extracted with ethyl acetate. The ethyl acetate layer was washed with brine and then dried with anhydrous sodium sulfate. The solvent was removed by reduced-pressure distillation, and the resulting residue was purified by column chromatography on silica gel eluting with chloroform/acetone and further by washing resulting crystals with acetoneto obtain 9 mg of the title compound (yield: 10%).

Workup

  1. extractionthe resulting admixture was extracted with ethyl acetate
  2. washThe ethyl acetate layer was washed with brine
  3. dry with materialdried with anhydrous sodium sulfate
  4. customThe solvent was removed by reduced-pressure distillation
  5. customthe resulting residue was purified by column chromatography on silica gel eluting with chloroform/acetone
  6. washfurther by washing
  7. customresulting crystals with acetoneto

Sources & evidence

ORD record
ord-a29bbbabb8de423289afeca205e1d993
Source dataset
uspto-grants-2000_11
Patent number
US06143764

Reaction notes

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