Sodium hydride → 4-{[7-(Benzyloxy)-6-methoxy-4-quinolyl]oxy}-2,3-dimethylaniline

HRID 1375767Notes

Reaction equation

HRID 1375767 reaction equation
[H-].[Na+].[NH2:3][C:4]1[CH:9]=[CH:8][C:7]([OH:10])=[C:6]([CH3:11])[C:5]=1[CH3:12].[CH2:13]([O:20][C:21]1[CH:30]=[C:29]2[C:24]([C:25](Cl)=[CH:26][CH:27]=[N:28]2)=[CH:23][C:22]=1[O:32][CH3:33])[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1.C(=O)([O-])O.[Na+]>CS(C)=O>[CH2:13]([O:20][C:21]1[CH:30]=[C:29]2[C:24]([C:25]([O:10][C:7]3[CH:8]=[CH:9][C:4]([NH2:3])=[C:5]([CH3:12])[C:6]=3[CH3:11])=[CH:26][CH:27]=[N:28]2)=[CH:23][C:22]=1[O:32][CH3:33])[C:14]1[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=1

Participants

6

Reactant 4

HCID 24758Sodium hydrideHCID 765424-HydroxyxylidineHCID 516892Sodium BicarbonateHCID 226465627-(Benzyloxy)-4-chloro-6-methoxyquinoline

Product 1

HCID 226671504-{[7-(Benzyloxy)-6-methoxy-4-quinolyl]oxy}-2,3-dimethylanilineYield 49%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

Sodium hydride (60 wt %, 0.32 g) was added to dimethyl sulfoxide (6 ml), and the mixture was stirred at room temperature for 30 min. 4-Amino-2,3-dimethylphenol (1.10 g) was then added thereto, and the mixture was stirred at room temperature for 10 min. Next, 7-(benzyloxy)-4-chloro-6-methoxyquinoline (1.20 g) was added thereto, and the mixture was stirred at 110° C. for 6 hr. A saturated aqueous sodium hydrogencarbonate solution was added to the reaction solution, followed by extraction with chloroform. The chloroform layer was dried over anhydrous magnesium sulfate. The solvent was removed by distillation under the reduced pressure, and the residue was purified by chromatography on silica gel by development with chloroform/acetone (6/1) to give 0.78 g (yield 49%) of the title compound.

Workup

  1. stirringthe mixture was stirred at room temperature for 10 min
  2. stirringthe mixture was stirred at 110° C. for 6 hr
  3. extractionfollowed by extraction with chloroform
  4. dry with materialThe chloroform layer was dried over anhydrous magnesium sulfate
  5. customThe solvent was removed by distillation under the reduced pressure
  6. customthe residue was purified by chromatography on silica gel by development with chloroform/acetone (6/1)

Sources & evidence

ORD record
ord-86d49f0fac4b46edb4730ae31e6ef456
Source dataset
uspto-grants-2007_01
Patent number
US07169789B2

Reaction notes

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