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

HRID 1505052Notes

Reaction equation

HRID 1505052 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-75cf3604edb747bb906c76e830fbe3f5
Source dataset
uspto-grants-2015_12
Patent number
US09216964B2

Reaction notes

Loading…