Potassium Hydroxide → HCID 22132713, compound

HRID 1857156Notes

Reaction equation

HRID 1857156 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]([O:31]C(=O)C)=[CH:27][CH:26]=2)=[O:24])=[CH:18][CH:17]=1.[OH-].[K+]>CO>[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]([OH:31])=[CH:27][CH:26]=2)=[O:24])=[CH:20][CH:21]=1

Participants

4

Reactant 2

HCID 14797Potassium HydroxideHCID 22132696HCID 22132696, compound

Product 1

HCID 22132713HCID 22132713, compoundYield 82.3%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

N-{4-[(6,7-Dimethoxy-4-quinolinyl)oxy]phenyl}-(4-acetoxyphenyl)carboxamide (103 mg) was dissolved in methanol (4 ml), 35% aqueous potassium hydroxide (2 ml) was added, and the admixture was stirred at room temperature for 5 hours. The reaction mixture was partitioned with ethyl acetate/water, and 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 crystals were washed with ether to obtain 77 mg of the title compound (yield: 82%).

Workup

  1. customThe reaction mixture was partitioned with ethyl acetate/water
  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. washthe resulting crystals were washed with ether

Sources & evidence

ORD record
ord-abbffbae034f45cd8c5ed1a2c630fc01
Source dataset
uspto-grants-2000_11
Patent number
US06143764

Reaction notes

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