Potassium Carbonate → Methyl 6-Methylpyridine-2-carboxylate N-oxide

HRID 2086259Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2086259
Cl.[CH3:2][C:3]1[N:8]=[C:7]([C:9]([O:11][CH3:12])=[O:10])[CH:6]=[CH:5][CH:4]=1.ClC1C=CC=C(C(OO)=[O:21])C=1.S([O-])([O-])=O.[Na+].[Na+].C(=O)([O-])[O-].[K+].[K+]>ClCCl>[CH3:2][C:3]1[CH:4]=[CH:5][CH:6]=[C:7]([C:9]([O:11][CH3:12])=[O:10])[N+:8]=1[O-:21]

Komponenten

6

Edukt 4

HCID 11430Potassium CarbonateHCID 24437Sodium SulfiteHCID 70297m-Chloroperbenzoic acidHCID 22727112Methyl 6-methylpyridine-2-carboxylate hydrochloride

Produkt 1

HCID 69545912Methyl 6-Methylpyridine-2-carboxylate N-oxideAusbeute 44,3 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Reaktionsbedingungen

Temperatur
50 °C

Versuchsvorschrift

A mixture of methyl 6-methylpyridine-2-carboxylate hydrochloride (5.8 g) and m-chloroperbenzoic acid (15.24 g) in dichloromethane (200 ml) was stirred at room temperature for 20 hours and 50° C. for 6 hours. After adding a small amount of sodium sulfite at 0° C., an aqueous solution of potassium carbonate was added to make the solution basic. The mixture was extracted with dichloromethane, and the organic phase was dried and concentrated. The resultant residue was purified by a column chromatography on a silica gel (ethyl acetate:hexane=5:1 to ethyl acetate:methanol=20:1) to obtain the title compound (2.29 g) as a tan oil.

Aufarbeitung

  1. extractionThe mixture was extracted with dichloromethane
  2. customthe organic phase was dried
  3. concentrationconcentrated
  4. customThe resultant residue was purified by a column chromatography on a silica gel (ethyl acetate:hexane=5:1 to ethyl acetate:methanol=20:1)

Quellen und Nachweise

ORD-Eintrag
ord-5af467c0fe7b48f39cbe7eeb7d37259e
Quelldatensatz
uspto-grants-2004_04
Patentnummer
US06723722B1

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