m-Chloroperbenzoic acid → HCID 68379690, compound
Reaction equation
[Br:1][C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[N:5]=[C:4]([C:12]([NH:14][C@H:15]2[CH2:20][CH2:19][CH2:18][CH2:17][C@@H:16]2[OH:21])=[O:13])[CH:3]=1.ClC1C=CC=C(C(OO)=[O:30])C=1>C(Cl)Cl>[Br:1][C:2]1[CH:3]=[C:4]([C:12]([NH:14][C@H:15]2[CH2:20][CH2:19][CH2:18][CH2:17][C@@H:16]2[OH:21])=[O:13])[N+:5]([O-:30])=[C:6]2[C:11]=1[CH:10]=[CH:9][CH:8]=[CH:7]2Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Procedure
To a solution of 4-bromo-N-[(1S,2S)-2-hydroxycyclohexyl]quinoline-2-carboxamide (0.20 g, 0.57 mmol) in 3.0 mL CH2Cl2 at room temperature was added 3-chloroperbenzoic acid (0.20 g, 1.15 mmol). The reaction mixture was stirred at room temperature for 18 h. Additional 3-chloroperbenzoic acid (0.20 g, 1.15 mmol) was added to reaction mixture and was stirred at room temperature for an additional 18 h. The reaction mixture was concentrated, and the resultant residue was subjected to silica gel chromatography eluting with 0-75% ethyl acetate in hexanes to afford 4-bromo-N-[(1S,2S)-2-hydroxycyclohexyl]quinoline-2-carboxamide 1-oxide that gave a mass ion (ES+) of 367.1 for (81Br) for M+H+.