Dimethyl Sulfoxide → 4-{[7-(Benzyloxy)-6-methoxy-4-quinolyl]oxy}-2-chloroaniline

HRID 1008327Notes

Reaction equation

HRID 1008327 reaction equation
[H-].[Na+].CS(C)=O.Cl.[NH2:8][C:9]1[CH:14]=[CH:13][C:12]([OH:15])=[CH:11][C:10]=1[Cl:16].[CH2:17]([O:24][C:25]1[CH:34]=[C:33]2[C:28]([C:29](Cl)=[CH:30][CH:31]=[N:32]2)=[CH:27][C:26]=1[O:36][CH3:37])[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1>O>[CH2:17]([O:24][C:25]1[CH:34]=[C:33]2[C:28]([C:29]([O:15][C:12]3[CH:13]=[CH:14][C:9]([NH2:8])=[C:10]([Cl:16])[CH:11]=3)=[CH:30][CH:31]=[N:32]2)=[CH:27][C:26]=1[O:36][CH3:37])[C:18]1[CH:19]=[CH:20][CH:21]=[CH:22][CH:23]=1

Participants

6

Reactant 4

HCID 679Dimethyl SulfoxideHCID 24758Sodium hydrideHCID 125981904-Amino-3-chlorophenol hydrochlorideHCID 226465627-(Benzyloxy)-4-chloro-6-methoxyquinoline

Product 1

HCID 226670624-{[7-(Benzyloxy)-6-methoxy-4-quinolyl]oxy}-2-chloroanilineYield 66%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
60 °C

Procedure

Sodium hydride (60 wt %, 320 mg) was added to dimethyl sulfoxide (3.6 ml), and the mixture was stirred at 60° C. for 30 min and was then cooled to room temperature. Next, 4-amino-3-chlorophenol hydrochloride (720 mg) was added thereto, and the mixture was stirred at room temperature for 10 min. 7-(Benzyloxy)-4-chloro-6-methoxyquinoline (600 mg) was then added thereto, and the mixture was stirred at 105° C. for 22 hr. Water was added to the reaction solution, followed by extraction with chloroform. The chloroform layer was then washed with a saturated aqueous sodium hydrogencarbonate solution and was dried over anhydrous sodium sulfate. The solvent was removed by distillation under the reduced pressure, and methanol was added to the residue to prepare a suspension. The precipitated crystal was collected by suction filtration to give 533 mg (yield 66%) of the title compound.

Workup

  1. temperaturewas then cooled to room temperature
  2. stirringthe mixture was stirred at room temperature for 10 min
  3. stirringthe mixture was stirred at 105° C. for 22 hr
  4. extractionfollowed by extraction with chloroform
  5. washThe chloroform layer was then washed with a saturated aqueous sodium hydrogencarbonate solution
  6. dry with materialwas dried over anhydrous sodium sulfate
  7. customThe solvent was removed by distillation under the reduced pressure, and methanol
  8. additionwas added to the residue
  9. customto prepare a suspension
  10. filtrationThe precipitated crystal was collected by suction filtration

Sources & evidence

ORD record
ord-eba7ab663fed4984a16ac356198218fa
Source dataset
uspto-grants-2004_09
Patent number
US06797823B1

Reaction notes

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