m-Chloroperbenzoic acid → HCID 54080876, compound

HRID 1419868Notes

Reaction equation

HRID 1419868 reaction equation
[C:1]([C:5]1[CH:6]=[N:7][C:8]2[C:13]([C:14]=1[NH:15][C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][C:17]=1[CH3:22])=[CH:12][CH:11]=[CH:10][C:9]=2[O:23][CH2:24][CH2:25][S:26][CH2:27][CH2:28][CH3:29])(=[O:4])[CH2:2][CH3:3].C(=O)(O)[O-:31].[Na+].C1C=C(Cl)C=C(C(OO)=O)C=1>C(Cl)Cl.O>[C:1]([C:5]1[CH:6]=[N:7][C:8]2[C:13]([C:14]=1[NH:15][C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][C:17]=1[CH3:22])=[CH:12][CH:11]=[CH:10][C:9]=2[O:23][CH2:24][CH2:25][S:26]([CH2:27][CH2:28][CH3:29])=[O:31])(=[O:4])[CH2:2][CH3:3]

Participants

6

Reactant 3

HCID 70297m-Chloroperbenzoic acidHCID 516892Sodium BicarbonateHCID 54029568HCID 54029568, compound

Product 1

HCID 54080876HCID 54080876, compoundYield 73.4%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent2×

Procedure

3-Propanoyl-4-(2-methylphenylamino)-8-(2-propylthioethoxy)quinoline (0.5 g, 1.22 mmol) was dissolved in 10 ml methylene chloride. A solution of sodium bicarbonate (250 mg, 3.0 mmol) in 10 ml water was added. The mixture was cooled to 2°-4° C. A solution of 70% m-CPBA (295 mg, 1.20 mmol) in 10 ml methylene chloride was added dropwise during 10 min. The temperature was allowed to rise to room temperature and the mixture was stirred 30 min at this temperature. The organic layer was dried over Na2SO4 and evaporated. The residue was purified by column chromatography (methylene chloride:ethanol 90:10) to give 380 mg (73%) of the title compound.

Workup

  1. temperatureThe mixture was cooled to 2°-4° C
  2. customto rise to room temperature
  3. dry with materialThe organic layer was dried over Na2SO4
  4. customevaporated
  5. customThe residue was purified by column chromatography (methylene chloride:ethanol 90:10)

Sources & evidence

ORD record
ord-3860b3edf315445c84fb9b5911e20016
Source dataset
uspto-grants-1999_03
Patent number
US05889021

Reaction notes

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