6-Hydroxyquinoline → Methyl 4-(6-quinolyloxy)-3-methylsulfonylbenzoate

HRID 376906Notes

Reaction equation

HRID 376906 reaction equation
Cl[C:2]1[CH:11]=[CH:10][C:5]([C:6]([O:8][CH3:9])=[O:7])=[CH:4][C:3]=1[S:12]([CH3:15])(=[O:14])=[O:13].[OH:16][C:17]1[CH:18]=[C:19]2[C:24](=[CH:25][CH:26]=1)[N:23]=[CH:22][CH:21]=[CH:20]2.C([O-])([O-])=O.[K+].[K+].C([O-])(O)=O.[Na+]>CN(C=O)C>[N:23]1[C:24]2[C:19](=[CH:18][C:17]([O:16][C:2]3[CH:11]=[CH:10][C:5]([C:6]([O:8][CH3:9])=[O:7])=[CH:4][C:3]=3[S:12]([CH3:15])(=[O:14])=[O:13])=[CH:26][CH:25]=2)[CH:20]=[CH:21][CH:22]=1

Participants

6

Reactant 4

HCID 113746-HydroxyquinolineHCID 11430Potassium CarbonateHCID 516892Sodium BicarbonateHCID 10490815Methyl 4-chloro-3-(methylsulfonyl)benzoate

Product 1

HCID 19360547Methyl 4-(6-quinolyloxy)-3-methylsulfonylbenzoate

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

2 mmol of methyl 4-chloro-3-methylsulfonylbenzoate, 2 mmol of 6-hydroxyquinoline and 6 mmol of K2CO3 were stirred at 130° C. for 2 h in 20 ml of DMF (anhydrous). The mixture was then poured into 100 ml of saturated aqueous NaHCO3 solution and extracted 3 times with 100 ml of EA. The extract was dried over Na2SO4, the solvent was removed in vacuo and the product was reacted further without further purification.

Workup

  1. extractionextracted 3 times with 100 ml of EA
  2. dry with materialThe extract was dried over Na2SO4
  3. customthe solvent was removed in vacuo
  4. customthe product was reacted further without further purification

Sources & evidence

ORD record
ord-71fa8c9e10a242cd8f2ee19a388c4e94
Source dataset
uspto-grants-2000_02
Patent number
US06022899

Reaction notes

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