m-Chloroperbenzoic acid → 3-ethoxyisoquinoline N-oxide

HRID 2405780

Reaktionsgleichung

Reaktionsgleichung von HRID 2405780
[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]

Komponenten

4

Edukt 2

HCID 70297m-Chloroperbenzoic acidHCID 6409663-Ethoxyisoquinoline

Produkt 1

HCID 686175523-ethoxyisoquinoline N-oxideAusbeute 69,9 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel2×

Versuchsvorschrift

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 it 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]+.

Aufarbeitung

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

Quellen und Nachweise

ORD-Eintrag
ord-de9bb94ac4514c35a73cfafe1ee4c486
Quelldatensatz
uspto-grants-2014_08
Patentnummer
US08809267B2

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