m-Chloroperbenzoic acid → 2-(2-Pyridylmethyl)-1H-isoindole-1,3(2H)-dione N-oxide

HRID 748324Notes

Reaction equation

HRID 748324 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

HCID 70297m-Chloroperbenzoic acidHCID 6172022-(2-Pyridinylmethyl)-1H-isoindole-1,3(2H)-dione

Product 1

HCID 865964682-(2-Pyridylmethyl)-1H-isoindole-1,3(2H)-dione N-oxideYield 99%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

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).

Workup

  1. customThe solvent was evaporated
  2. washthe residue was washed with ethyl acetate

Sources & evidence

ORD record
ord-3584b15cce1b45b6a3d0a3f7908ac5e5
Source dataset
uspto-grants-2008_07
Patent number
US07399759B2

Reaction notes

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