6-Isopropylquinoline → 6-Isopropylquinoline 1-oxide

Reaction equation

[CH:1]([C:4]1[CH:5]=[C:6]2[C:11](=[CH:12][CH:13]=1)[N:10]=[CH:9][CH:8]=[CH:7]2)([CH3:3])[CH3:2].ClC1C=CC=C(C(OO)=[O:22])C=1.C(=O)([O-])O.[Na+]>C(Cl)(Cl)Cl>[CH:1]([C:4]1[CH:5]=[C:6]2[C:11](=[CH:12][CH:13]=1)[N+:10]([O-:22])=[CH:9][CH:8]=[CH:7]2)([CH3:3])[CH3:2]

Participants

Procedure

To 40 mL of a chloroform solution containing 2.0 g of 6-isopropylquinoline, 2.9 g of m-chloroperbenzoic acid was added, and the mixture was stirred at room temperature overnight. Thereto was added an aqueous saturated sodium hydrogen carbonate solution, the organic layer was separated, and the aqueous layer was extracted with chloroform. The organic layer and the extract were combined, and the resultant solution was washed with an aqueous saturated sodium chloride solution and dried over anhydrous magnesium sulfate, and the solvent was removed under reduced pressure to obtain 2.1 g of a brown oily substance, 6-isopropylquinoline N-oxide.