m-Chloroperbenzoic acid → HCID 54154290, compound

HRID 1419870Notes

Reaction equation

HRID 1419870 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][CH2:26][S:27][CH2:28][CH2:29][CH3:30])(=[O:4])[CH2:2][CH3:3].C(=O)(O)[O-:32].[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][CH2:26][S:27]([CH2:28][CH2:29][CH3:30])=[O:32])(=[O:4])[CH2:2][CH3:3]

Participants

6

Reactant 3

HCID 70297m-Chloroperbenzoic acidHCID 516892Sodium BicarbonateHCID 54548203HCID 54548203, compound

Product 1

HCID 54154290HCID 54154290, compoundYield 77.6%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent2×

Procedure

3-Propanoyl-4-(2-methylphenylamino)-8-(3-propylthiopropoxy)quinoline (200 mg, 0.47 mmol) was dissolved in 5 ml methylene chloride. A solution of sodium bicarbonate (80 mg, 0.95 mmol) in 5 ml water was added. The mixture was cooled to 2°-4° C. A solution of 70% m-CPBA (115mg, 0.47 mmol) in 5 ml methylene chloride was added dropwise during 10 min. The temperature was allowed to rise and the mixture was stirred for 30 min at room temperature. The methylene chloride layer was separated and washed with water. The organic layer was then dried over Na2SO4 and evaporated. The crude product was purified by column chromatography (methylene chloride: ethanol 95:5). 160 mg (77%) of the title compound was obtained.

Workup

  1. temperatureThe mixture was cooled to 2°-4° C
  2. customThe methylene chloride layer was separated
  3. washwashed with water
  4. dry with materialThe organic layer was then dried over Na2SO4
  5. customevaporated
  6. customThe crude product was purified by column chromatography (methylene chloride: ethanol 95:5)

Sources & evidence

ORD record
ord-738e2358ae6944ee88b5b1074bb2574c
Source dataset
uspto-grants-1999_03
Patent number
US05889021

Reaction notes

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