m-Chloroperbenzoic acid → 2-Chloro-4-methylpyridine 1-oxide

HRID 37852

Reaktionsgleichung

Reaktionsgleichung von HRID 37852
ClC1C=CC=C(C(OO)=[O:9])C=1.[Cl:12][C:13]1[CH:18]=[C:17]([CH3:19])[CH:16]=[CH:15][N:14]=1>C(Cl)(Cl)Cl>[Cl:12][C:13]1[CH:18]=[C:17]([CH3:19])[CH:16]=[CH:15][N+:14]=1[O-:9]

Komponenten

4

Edukt 2

HCID 70297m-Chloroperbenzoic acidHCID 772482-Chloro-4-methylpyridine

Produkt 1

HCID 124874842-Chloro-4-methylpyridine 1-oxideAusbeute 464,3 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6212ChloroformLösungsmittel

Versuchsvorschrift

40% meta-chloroperbenzoic acid (13.5 g, 31.4 mmol) was added at ambient temperature to a solution of 2-chloro-4-methyl-pyridine (2.0 g, 1.5 mmol) in chloroform (20 mL) and heated at reflux for 24 h. After allowing to cool, the mixture was washed with water followed by sodium bicarbonate solution. The separated organic phase was further washed with water and brine, dried over anhydrous sodium sulfate and concentrated to give a residue which was purified by column chromatography over silica gel (60-120 mesh) using 10% methanol in ethyl acetate as eluent to afford 2-chloro-4-methyl-pyridine 1-oxide (1.0 g, 45%) as a deep brown oily liquid.

Aufarbeitung

  1. temperatureheated
  2. temperatureat reflux for 24 h
  3. temperatureto cool
  4. washthe mixture was washed with water
  5. washThe separated organic phase was further washed with water and brine
  6. dry with materialdried over anhydrous sodium sulfate
  7. concentrationconcentrated
  8. customto give a residue which
  9. customwas purified by column chromatography over silica gel (60-120 mesh)

Quellen und Nachweise

ORD-Eintrag
ord-c2ddec53bd744cd7b5a933c42f3d5d64
Quelldatensatz
uspto-grants-2013_09
Patentnummer
US08524705B2

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