m-Chloroperbenzoic acid → Isoquinoline, 4-cyclopropyl-, 2-oxide

HRID 1852213Notes

Reaction equation

HRID 1852213 reaction equation
[CH:1]1([C:4]2[C:13]3[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=3)[CH:7]=[N:6][CH:5]=2)[CH2:3][CH2:2]1.C1C=C(Cl)C=C(C(OO)=[O:22])C=1>C(Cl)Cl>[CH:1]1([C:4]2[C:13]3[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=3)[CH:7]=[N+:6]([O-:22])[CH:5]=2)[CH2:3][CH2:2]1

Participants

4

Reactant 2

HCID 70297m-Chloroperbenzoic acidHCID 12032144Isoquinoline, 4-cyclopropyl-

Product 1

HCID 86683265Isoquinoline, 4-cyclopropyl-, 2-oxideYield 80%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a solution of 4-cyclopropylisoquinoline (0.4 g, 2.364 mmol) in DCM (10 ml) was added m-CPBA (1.224 g, 7.09 mmol) at room temperature. The reaction mass was stirred at the same temperature for 18 h. The reaction mass was diluted with DCM and washed with water and aqueous sodium bicarbonate solution. The combined organic layer was dried over anhydrous Na2SO4 and evaporated under reduced pressure to get desired compound (0.35 g, 80%) as solid. The crude compound was taken further without purification.

Workup

  1. washwashed with water and aqueous sodium bicarbonate solution
  2. dry with materialThe combined organic layer was dried over anhydrous Na2SO4
  3. customevaporated under reduced pressure

Sources & evidence

ORD record
ord-d49eff751acf483f92974daf031eb141
Source dataset
uspto-grants-2015_02
Patent number
US08957203B2

Reaction notes

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