m-Chloroperbenzoic acid → 1H-Isoindole-1,3(2H)-dione, 2-(4,5-dimethyl-1-oxido-2-pyridinyl)-

HRID 869891Notes

Reaction equation

HRID 869891 reaction equation
[CH3:1][C:2]1[C:7]([CH3:8])=[CH:6][N:5]=[C:4]([N:9]2[C:17](=[O:18])[C:16]3[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=3)[C:10]2=[O:19])[CH:3]=1.C1C=C(Cl)C=C(C(OO)=[O:28])C=1>C(Cl)Cl>[O:18]=[C:17]1[C:16]2[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=2)[C:10](=[O:19])[N:9]1[C:4]1[CH:3]=[C:2]([CH3:1])[C:7]([CH3:8])=[CH:6][N+:5]=1[O-:28]

Participants

4

Reactant 2

HCID 70297m-Chloroperbenzoic acidHCID 687404972-(4,5-Dimethyl-2-pyridinyl)-1H-isoindole-1,3(2H)-dione

Product 1

HCID 687387371H-Isoindole-1,3(2H)-dione, 2-(4,5-dimethyl-1-oxido-2-pyridinyl)-Yield 83%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 2-(4,5-dimethylpyridin-2-yl)-isoindoline-1,3-dione (1.7 g, 0.01 mol) in CH2Cl2 (50 mL) was added m-CPBA (3.5 g, 0.02 mol) at the room temperature. The mixture was stirred overnight, then quenched by addition of a saturated solution of Na2S2O3 (100 mL). The organic layer was separated and the aqueous phase was extracted with CH2Cl2 (50 mL×3). The combined organic layers were dried over anhydrous Na2SO4, filtered and evaporated under vacuum to give 2-(1,3-dioxoisoindolin-2-yl)-4,5-dimethylpyridine 1-oxide (1.5 g, 83%), which was used directly in the next step.

Workup

  1. customquenched by addition of a saturated solution of Na2S2O3 (100 mL)
  2. customThe organic layer was separated
  3. extractionthe aqueous phase was extracted with CH2Cl2 (50 mL×3)
  4. dry with materialThe combined organic layers were dried over anhydrous Na2SO4
  5. filtrationfiltered
  6. customevaporated under vacuum

Sources & evidence

ORD record
ord-2211658c327f44728ae38fe8133e607e
Source dataset
uspto-grants-2015_03
Patent number
US08969386B2

Reaction notes

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