Sodium hydride → HCID 21890974, compound

HRID 721617Notes

Reaction equation

HRID 721617 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]([OH:22])=[CH:18][CH:17]=1.[H-].[Na+].COC1C=C2C(=CC=1OC)N=[CH:32][CH:31]=[C:30]2[O:39][C:40]1[CH:45]=[CH:44][C:43](NC(NC2CCNCC2)=O)=[CH:42][CH:41]=1.[C:56](=O)([O-])[OH:57].[Na+]>CN(C)C=O>[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]([O:22][CH2:32][CH2:31][CH2:30][O:39][C:40]2[CH:41]=[CH:42][CH:43]=[CH:44][C:45]=2[O:57][CH3:56])=[CH:20][CH:21]=1

Participants

6

Reactant 4

HCID 24758Sodium hydrideHCID 516892Sodium BicarbonateHCID 17755508HCID 17755508, compoundHCID 21890637HCID 21890637, compound

Product 1

HCID 21890974HCID 21890974, compoundYield 75%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

4-[(6,7-Dimethoxy-4-quinolyl)oxy]phenol (100 mg) was dissolved in dimethylformamide (2 ml) to prepare a solution. Sodium hydride (16 mg) was then added to the solution, and the mixture was stirred at room temperature for 10 min. A solution of the compound (1) (91 mg) in dimethylformamide was added thereto, and the mixture was further stirred at room temperature for 6 hr. A saturated aqueous sodium hydrogencarbonate solution was added to the reaction solution, and the mixture was extracted with ethyl acetate, followed by washing three times with saturated brine. The extract was then dried over anhydrous sodium sulfate. The solvent was removed by distillation under the reduced pressure. The residue was purified by thin-layer chromatography using chloroform/methanol for development to give the title compound (116 mg, yield 75%).

Workup

  1. customto prepare a solution
  2. stirringthe mixture was further stirred at room temperature for 6 hr
  3. extractionthe mixture was extracted with ethyl acetate
  4. washby washing three times with saturated brine
  5. dry with materialThe extract was then dried over anhydrous sodium sulfate
  6. customThe solvent was removed by distillation under the reduced pressure
  7. customThe residue was purified by thin-layer chromatography

Sources & evidence

ORD record
ord-dd91aa4d86a648bcb75102f3935275e3
Source dataset
uspto-grants-2006_11
Patent number
US07135466B2

Reaction notes

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