m-Chloroperbenzoic acid → 2-(1,3-Dioxoisoindolin-2-yl)-5-methylpyridine 1-oxide

HRID 1890740Notes

Reaction equation

HRID 1890740 reaction equation
[CH3:1][C:2]1[CH:3]=[CH:4][C:5]([N:8]2[C:16](=[O:17])[C:15]3[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=3)[C:9]2=[O:18])=[N:6][CH:7]=1.C1C=C(Cl)C=C(C(OO)=[O:27])C=1>C(Cl)Cl>[O:17]=[C:16]1[C:15]2[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=2)[C:9](=[O:18])[N:8]1[C:5]1[CH:4]=[CH:3][C:2]([CH3:1])=[CH:7][N+:6]=1[O-:27]

Participants

4

Reactant 2

HCID 70297m-Chloroperbenzoic acidHCID 109665522-(5-Methylpyridin-2-yl)isoindoline-1,3-dione

Product 1

HCID 672124072-(1,3-Dioxoisoindolin-2-yl)-5-methylpyridine 1-oxide

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a solution of 2-(5-methylpyridin-2-yl)isoindoline-1,3-dione (1.62 g, 6.8 mmol) in DCM (32 ml) is added mCPBA (4.1 g, 18.2 mmol) in small portions at room temperature, and the solution is then stirred at room temperature overnight. The solution is diluted with dichloromethane, washed with aqueous Na2CO3 solution, dried over Na2SO4 and concentrated to afford 2-(1,3-dioxoisoindolin-2-yl)-5-methylpyridine 1-oxide as a brown solid. It is used without further purification in the next step. LC-MS m/z: 254.1 (M+1).

Workup

  1. washwashed with aqueous Na2CO3 solution
  2. dry with materialdried over Na2SO4
  3. concentrationconcentrated

Sources & evidence

ORD record
ord-a7d156692b9c4a9f8512104e9c1175e8
Source dataset
uspto-grants-2013_08
Patent number
US08507491B2

Reaction notes

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