m-Chloroperbenzoic acid → HCID 53678886, compound

HRID 1419862Notes

Reaction equation

HRID 1419862 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][CH3:27])(=[O:4])[CH2:2][CH3:3].C([O-])(O)=[O:29].[Na+].C1C=C(Cl)C=C(C(OO)=O)C=1>C(Cl)Cl>[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]([CH3:27])=[O:29])(=[O:4])[CH2:2][CH3:3]

Participants

5

Reactant 3

HCID 70297m-Chloroperbenzoic acidHCID 516892Sodium BicarbonateHCID 53940201HCID 53940201, compound

Product 1

HCID 53678886HCID 53678886, compoundYield 48.5%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Conditions

Temperature
4 °C

Procedure

3-Propanoyl-4-(2-methylphenylamino)-8-(2-methylthioethoxy)quinoline (0.10 g, 0.26 mmol) was dissolved in methylene chloride (5 ml). NaHCO3 (45 mg) in H2 0 (5 ml) was added. The mixture was cooled to 4° C. A solution of 71% m-CPBA (0.062 g, 0.25 mmol) in methylene chloride (5 ml) was added dropwise. After stirring for 1 h at 2°-4° C., the organic layer was washed with a saturated sodium bicarbonate solution. The organic layer was dried over sodium sulfate and evaporated. Chromatography (SiO2 ; CH2Cl2 :EtOH 90:10) gave 50 mg (48%) of the desired product.

Workup

  1. washthe organic layer was washed with a saturated sodium bicarbonate solution
  2. dry with materialThe organic layer was dried over sodium sulfate
  3. customevaporated

Sources & evidence

ORD record
ord-e74382242d19420198c8a35ad6e35e91
Source dataset
uspto-grants-1999_03
Patent number
US05889021

Reaction notes

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