m-Chloroperbenzoic acid → 3-Chloromethyl-2-methyl-pyridine 1-oxide

HRID 1681

Reaktionsgleichung

Reaktionsgleichung von HRID 1681
[Cl:1][CH2:2][C:3]1[C:4]([CH3:9])=[N:5][CH:6]=[CH:7][CH:8]=1.ClC1C=C(C=CC=1)C(OO)=[O:15]>C(Cl)(Cl)Cl>[Cl:1][CH2:2][C:3]1[C:4]([CH3:9])=[N+:5]([O-:15])[CH:6]=[CH:7][CH:8]=1

Komponenten

4

Edukt 2

HCID 70297m-Chloroperbenzoic acidHCID 122437113-(Chloromethyl)-2-methylpyridine

Produkt 1

HCID 220536063-Chloromethyl-2-methyl-pyridine 1-oxide

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6212ChloroformLösungsmittel

Versuchsvorschrift

To a stirred solution of 3-chloromethyl-2-methylpyridine from Step 2 above (0.50 g; 3.5 mmol) in CHCl3 (40 mL) was added m-chloroperoxybenzoic acid (1.1 g of 55:45 mCPBA:mCBA; 3.5 mmol). After 1.5 h, TLC analysis indicated complete conversion to a lower Rf product. The solution was extracted with equal volumes of saturated aqueous NaHCO3 and water, dried (MgSO4), filtered, and evaporated under reduced pressure. The residue was purified by pressurized silica gel column chromatography using 97:3 CH2Cl2 :MeOH as eluant. 3-Chloromethyl-2-methylpyridine N-oxide was obtained as a solid (TLC: Rf =0.30 (97:3 CH2Cl2 :MeOH); FAB MS m/z 158 (M+ +H)).

Aufarbeitung

  1. extractionThe solution was extracted with equal volumes of saturated aqueous NaHCO3 and water
  2. dry with materialdried (MgSO4)
  3. filtrationfiltered
  4. customevaporated under reduced pressure
  5. customThe residue was purified by pressurized silica gel column chromatography

Quellen und Nachweise

ORD-Eintrag
ord-b8dbba8e74ff4118bc3513f530757669
Quelldatensatz
uspto-grants-1998_03
Patentnummer
US05726172

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