m-Chloroperbenzoic acid → HCID 3710254, compound

HRID 588372Notes

Reaction equation

HRID 588372 reaction equation
[Cl:1][C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[CH:5]=[CH:4][N:3]=1.C1C=C(Cl)C=C(C(OO)=[O:20])C=1>C(Cl)Cl>[Cl:1][C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[CH:5]=[CH:4][N+:3]=1[O-:20]

Participants

4

Reactant 2

HCID 70297m-Chloroperbenzoic acidHCID 140539Isoquinoline, 1-chloro-

Product 1

HCID 3710254HCID 3710254, compoundYield 37.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a solution of 1-chloroisoquinoline (3.0 g, 18 mmol) in DCM (50 mL) was added m-CPBA (9.5 g, 55 mmol). The mixture was stirred at room temperature for 48 h. The mixture was diluted with DCM, and then washed with brine, dried over Na2SO4, filtered, and the filtrate was concentrated under reduced pressure. The resulting residue was purified by silica gel flash column chromatography eluting with a gradient of petroleum ether: EtOAc (5:1 to 0:1) to afford the title compound (1.2 g, 36%) as a yellow solid.

Workup

  1. washwashed with brine
  2. dry with materialdried over Na2SO4
  3. filtrationfiltered
  4. concentrationthe filtrate was concentrated under reduced pressure
  5. customThe resulting residue was purified by silica gel flash column chromatography
  6. washeluting with a gradient of petroleum ether: EtOAc (5:1 to 0:1)

Sources & evidence

ORD record
ord-38bd6db4e8224302b09650cff355001d
Source dataset
uspto-grants-2016_01
Patent number
US09227956B2

Reaction notes

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