4-Toluenesulfonyl chloride → p-Toluenesulfonic acid [4-(benzyloxy)-3-methylquinolin-2-yl]methyl ester

HRID 384433Notes

Reaction equation

HRID 384433 reaction equation
[CH2:1]([O:8][C:9]1[C:18]2[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=2)[N+:12]([O-])=[C:11]([CH3:20])[C:10]=1[CH3:21])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(=O)([O-])[O-:23].[K+].[K+].[C:28]1([CH3:38])[CH:33]=[CH:32][C:31]([S:34](Cl)(=[O:36])=[O:35])=[CH:30][CH:29]=1>C(#N)C>[CH2:1]([O:8][C:9]1[C:18]2[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=2)[N:12]=[C:11]([CH2:20][O:35][S:34]([C:31]2[CH:32]=[CH:33][C:28]([CH3:38])=[CH:29][CH:30]=2)(=[O:23])=[O:36])[C:10]=1[CH3:21])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 73974-Toluenesulfonyl chlorideHCID 11430Potassium CarbonateHCID 107077894-Benzyloxy-2,3-dimethylquinoline-1-oxide

Product 1

HCID 59527351p-Toluenesulfonic acid [4-(benzyloxy)-3-methylquinolin-2-yl]methyl esterYield 40.7%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To a mixture of 4-benzyloxy-2,3-dimethylquinoline-1-oxide (21.2 g), potassium carbonate (20.9 g), and acetonitrile (400 mL) was added p-toluenesulfonyl chloride (18.8 g), followed by stirring at room temperature for 12 hours. Insolubles were removed by filtration, and the filtrate was concentrated under reduced pressure. Water (500 mL) was added to the residue, followed by twice extractions with ethyl acetate (500 mL). The organic layer was washed with saturated brine and then dried over anhydrous magnesium sulfate. The solvent was evaporated under reduced pressure, and the residue was purified by silica gel column chromatography (eluent: hexane/ethyl acetate=5/1) to obtain p-toluenesulfonic acid [4-(benzyloxy)-3-methylquinolin-2-yl]methyl ester (13.4 g).

Workup

  1. customInsolubles were removed by filtration
  2. concentrationthe filtrate was concentrated under reduced pressure
  3. additionWater (500 mL) was added to the residue
  4. extractionfollowed by twice extractions with ethyl acetate (500 mL)
  5. washThe organic layer was washed with saturated brine
  6. dry with materialdried over anhydrous magnesium sulfate
  7. customThe solvent was evaporated under reduced pressure
  8. customthe residue was purified by silica gel column chromatography (eluent: hexane/ethyl acetate=5/1)

Sources & evidence

ORD record
ord-d435d26f9e9448a59196f79a69f7de66
Source dataset
uspto-grants-2013_02
Patent number
US08367702B2

Reaction notes

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