m-Chloroperbenzoic acid → Methyl quinoline-6-carboxylate 1-oxide

HRID 2370777Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2370777
[N:1]1[C:10]2[C:5](=[CH:6][C:7]([C:11]([O:13][CH3:14])=[O:12])=[CH:8][CH:9]=2)[CH:4]=[CH:3][CH:2]=1.ClC1C=C(C=CC=1)C(OO)=[O:20]>C(Cl)Cl.C([O-])(O)=O.[Na+]>[CH3:14][O:13][C:11]([C:7]1[CH:6]=[C:5]2[C:10](=[CH:9][CH:8]=1)[N+:1]([O-:20])=[CH:2][CH:3]=[CH:4]2)=[O:12]

Komponenten

5

Edukt 2

HCID 70297m-Chloroperbenzoic acidHCID 736812Methyl quinoline-6-carboxylate

Produkt 1

HCID 21707072Methyl quinoline-6-carboxylate 1-oxide

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6344DichloromethaneLösungsmittelHCID 516892Sodium BicarbonateLösungsmittel

Versuchsvorschrift

To a solution of methyl quinoline-6-carboxylate from above in DCM (10 mL) was added 3-chlorobenzoperoxoic acid (1.991 g, 11.54 mmol). The reaction was stirred 21 h at rt. The mixture was then diluted with saturated aqueous NaHCO3 (40 mL), and the mixture was extracted with DCM (2×30 mL). The organic layers were combined, washed with saturated aqueous NaCl (40 mL), dried (MgSO4), and concentrated. The N-oxide was isolated as an orange solid which was used without purification in the next step.

Aufarbeitung

  1. extractionthe mixture was extracted with DCM (2×30 mL)
  2. washwashed with saturated aqueous NaCl (40 mL)
  3. dry with materialdried (MgSO4)
  4. concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag
ord-764c3d961af94eb8be792360676cc532
Quelldatensatz
uspto-grants-2014_04
Patentnummer
US08710043B2

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