m-Chloroperbenzoic acid → 3-Butyryl-4-(2-isopropylphenylamino)-8(2-methylsulfinylethoxy)quinoline

HRID 1419860Notes

Reaction equation

HRID 1419860 reaction equation
[C:1]([C:6]1[CH:7]=[N:8][C:9]2[C:14]([C:15]=1[NH:16][C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][C:18]=1[CH:23]([CH3:25])[CH3:24])=[CH:13][CH:12]=[CH:11][C:10]=2[O:26][CH2:27][CH2:28][S:29][CH3:30])(=[O:5])[CH2:2][CH2:3][CH3:4].C([O-])(O)=[O:32].[Na+].C1C=C(Cl)C=C(C(OO)=O)C=1>C(Cl)Cl.O>[C:1]([C:6]1[CH:7]=[N:8][C:9]2[C:14]([C:15]=1[NH:16][C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][C:18]=1[CH:23]([CH3:24])[CH3:25])=[CH:13][CH:12]=[CH:11][C:10]=2[O:26][CH2:27][CH2:28][S:29]([CH3:30])=[O:32])(=[O:5])[CH2:2][CH2:3][CH3:4]

Participants

6

Reactant 3

HCID 70297m-Chloroperbenzoic acidHCID 516892Sodium BicarbonateHCID 544957133-Butyryl-4-(2-isopropylphenylamino)-8-(2-methylthioethoxy)quinoline

Product 1

HCID 545372003-Butyryl-4-(2-isopropylphenylamino)-8(2-methylsulfinylethoxy)quinolineYield 57%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent2×

Procedure

3-Butyryl-4-(2-isopropylphenylamino)-8-(2-methylthioethoxy)quinoline (0.22 g, 0.52 mmol) was dissolved in methylene chloride (15 ml) and added to a mixture of 0.093g NaHCO3 in 15 ml H2O. A solution of 71% m-CPBA (0.12 g, 0.50 mmol) in 7 ml methylene chloride was added dropwise at 4° C. The solution was stirred for one hour at this temperature. The reaction mixture was washed with a saturated sodium bicarbonate solution. The organic layer was dried over Na2SO4 and evaporated. Chromatography with methylene chloride:methanol 10:1 as eluent gave 0.130 g (57%) of the desired product.

Workup

  1. washThe reaction mixture was washed with a saturated sodium bicarbonate solution
  2. dry with materialThe organic layer was dried over Na2SO4
  3. customevaporated

Sources & evidence

ORD record
ord-7ed11c8225cb485daaa3529bc5c95c72
Source dataset
uspto-grants-1999_03
Patent number
US05889021

Reaction notes

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