m-Chloroperbenzoic acid → 4-Methylisoquinoline 2-oxide

HRID 1852210Notes

Reaction equation

HRID 1852210 reaction equation
[CH3:1][C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[CH:5]=[N:4][CH:3]=1.C1C=C(Cl)C=C(C(OO)=[O:20])C=1>C(Cl)Cl>[CH3:1][C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[CH:5]=[N+:4]([O-:20])[CH:3]=1

Participants

4

Reactant 2

HCID 70297m-Chloroperbenzoic acidHCID 640939Isoquinoline, 4-methyl-

Product 1

HCID 229588294-Methylisoquinoline 2-oxideYield 97.5%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a solution of 4-methylisoquinoline (0.6 g, 4.19 mmol) in DCM (20 ml) was added m-CPBA (2.169 g, 12.57 mmol) at room temperature. The reaction mass was stirred at the same temperature for 18 h. The reaction mass was diluted with DCM and extracted with water. The combined organic layer was dried over anhydrous Na2SO4 and evaporated under reduced pressure to get desired compound (0.65 g, 88%) as a semi solid. The crude compound was taken further without purification.

Workup

  1. extractionextracted with water
  2. dry with materialThe combined organic layer was dried over anhydrous Na2SO4
  3. customevaporated under reduced pressure

Sources & evidence

ORD record
ord-68095ebeb1fb41e9beb633b3a4ec0292
Source dataset
uspto-grants-2015_02
Patent number
US08957203B2

Reaction notes

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