m-Chloroperbenzoic acid → 2-(2-Pyridylmethyl)-1H-isoindole-1,3(2H)-dione N-oxide
Reaction equation
[N:1]1[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[CH2:7][N:8]1[C:16](=[O:17])[C:15]2[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=2)[C:9]1=[O:18].ClC1C=CC=C(C(OO)=[O:27])C=1>C(Cl)(Cl)Cl>[N:1]1[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[CH2:7][N+:8]1([O-:27])[C:16](=[O:17])[C:15]2[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=2)[C:9]1=[O:18]Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Procedure
2-(2-Pyridylmethyl)-1H-isoindole-1,3(2H)-dione (7.5 g, 32 mmol) and 3-chloroperbenzoic acid (77%, 14.3 g, 64 mmol) were dissolved in chloroform (250 ml), and the mixture was stirred at room temperature for 20 hrs. The solvent was evaporated, and the residue was washed with ethyl acetate to give the titled compound (8.0 g, 99%) as white crystals. 1H-NMR (CDCl3) δ: 5.16 (2H, s), 7.15 (1H, m), 7.24-7.26 (2H, m) 7.77 (2H, m), 7.90 (2H, m), 8.33 (1H, m).