m-Chloroperbenzoic acid → 3-ethoxyisoquinoline N-oxide

HRID 1893631Notes

Reaction equation

HRID 1893631 reaction equation
[CH2:1]([O:3][C:4]1[N:5]=[CH:6][C:7]2[C:12]([CH:13]=1)=[CH:11][CH:10]=[CH:9][CH:8]=2)[CH3:2].C1C=C(Cl)C=C(C(OO)=[O:22])C=1>C(Cl)Cl>[CH2:1]([O:3][C:4]1[N+:5]([O-:22])=[CH:6][C:7]2[C:12]([CH:13]=1)=[CH:11][CH:10]=[CH:9][CH:8]=2)[CH3:2]

Participants

4

Reactant 2

HCID 70297m-Chloroperbenzoic acidHCID 6409663-Ethoxyisoquinoline

Product 1

HCID 686175523-ethoxyisoquinoline N-oxideYield 69.9%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

3-Ethoxyisoquinoline (1.5 g, 8.7 mmol) was taken up in DCM (45 mL) at 0° C. mCPBA (77%, 4.1 g, 18.3 mmol) was added slowly and the resulting solution allowed to warm to rt overnight. The reaction volume was doubled with additional DCM and washed with 1M NaOH. Following separation and extraction with DCM, the combined organics were washed with brine, dried over anhydrous MgSO4 and concentrated in vacuo to afford 3-ethoxyisoquinoline N-oxide (1.15 g, 69%) as a white low melting solid that was used without further purification. LCMS found 190.05 [M+H]+.

Workup

  1. additionwas added slowly
  2. washwashed with 1M NaOH
  3. customseparation and extraction with DCM
  4. washthe combined organics were washed with brine
  5. dry with materialdried over anhydrous MgSO4
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-7587edeb7d644d429f8f689c321a6f7c
Source dataset
uspto-grants-2013_08
Patent number
US08513186B2

Reaction notes

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