m-Chloroperbenzoic acid → 2-(Methoxycarbonyl)-3-methylpyridine 1-oxide

HRID 2201578Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2201578
[CH3:1][C:2]1[C:3]([C:8]([O:10][CH3:11])=[O:9])=[N:4][CH:5]=[CH:6][CH:7]=1.C1C=C(Cl)C=C(C(OO)=[O:20])C=1>C(Cl)Cl>[CH3:11][O:10][C:8]([C:3]1[C:2]([CH3:1])=[CH:7][CH:6]=[CH:5][N+:4]=1[O-:20])=[O:9]

Komponenten

4

Edukt 2

HCID 70297m-Chloroperbenzoic acidHCID 12264487Methyl 3-methylpyridine-2-carboxylate

Produkt 1

HCID 727140222-(Methoxycarbonyl)-3-methylpyridine 1-oxideAusbeute 79 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

A mixture of methyl 3-methylpicolinate (2 g, 14.8 mmol) and m-CPBA (3 g, 17.8 mmol) in DCM (35 mL) was stirred at RT overnight. Then the mixture was washed with NaHSO3 (a.q.) and concentrated in vacuum. The residue was purified by column chromatography (DCM:MeOH=200:1) to give the product of 2-(methoxycarbonyl)-3-methylpyridine 1-oxide (1.89 g, yield: 79%). 1H-NMR (CDCl3, 400 MHz) δ 8.05 (d, J=6.0 Hz, 1H), 7.18 (t, J=8.4 Hz, 1H), 7.10 (d, J=8.0 Hz, 1H), 3.95 (s, 3H), 2.23 (s, 3H). MS (M+H)+: 168.

Aufarbeitung

  1. washThen the mixture was washed with NaHSO3 (a.q.)
  2. concentrationconcentrated in vacuum
  3. customThe residue was purified by column chromatography (DCM:MeOH=200:1)

Quellen und Nachweise

ORD-Eintrag
ord-b40c89c2bfba4f2088bb4080541338d9
Quelldatensatz
uspto-grants-2016_06
Patentnummer
US09364482B2

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