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

HRID 1291703Notes

Reaction equation

HRID 1291703 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-c09907fa8480465d82c3503d5247e916
Source dataset
uspto-grants-1998_05
Patent number
US05753710

Reaction notes

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