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

HRID 1419858Notes

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[CH3:23])=[CH:13][CH:12]=[CH:11][C:10]=2[O:24][CH2:25][CH2:26][S:27][CH3:28])(=[O:5])[CH2:2][CH2:3][CH3:4].C1C=C(Cl)C=C(C(OO)=[O:37])C=1>C(Cl)Cl>[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[CH3:23])=[CH:13][CH:12]=[CH:11][C:10]=2[O:24][CH2:25][CH2:26][S:27]([CH3:28])=[O:37])(=[O:5])[CH2:2][CH2:3][CH3:4]

Participants

Conditions

Temperature: -20 °C

Procedure

3-Butyryl-4-(2-methylphenylamino)-8-(2-methylthioethoxy)quinoline (0.15 g, 0.38 mmol) was dissolved in methylene chloride (3 ml) and cooled to -20° C. A solution of 71% m-CPBA (0.089 g, 0.36 mmol) in 1 ml of methylene chloride was added dropwise. The temperature was allowed to rise to room temperature whereafter the solution was stirred for 15 min at room temperature. The reaction mixture was washed with a saturated sodium bicarbonate solution. The organic layer was dried over sodium sulfate and evaporated. Chromatography with methylene chloride:methanol 10:1 as the eluent gave 0.064 g (41%) of the desired product.

Workup

customto rise to room temperature whereafter the solution
washThe reaction mixture was washed with a saturated sodium bicarbonate solution
dry with materialThe organic layer was dried over sodium sulfate
customevaporated

Sources & evidence

ORD record: ord-9c6ba8c68e5445f9baf2a4e69c81f95e
Source dataset: uspto-grants-1999_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05889021

Reaction notes

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