Sodium Chloride → 2-Chloro-4,6-dimethylpyridine

HRID 37851

Reaktionsgleichung

Reaktionsgleichung von HRID 37851
N[C:2]1[CH:7]=[C:6]([CH3:8])[CH:5]=[C:4]([CH3:9])[N:3]=1.N([O-])=O.[Na+].[Cl-:14].[Na+].[OH-].[Na+]>Cl.O>[Cl:14][C:2]1[CH:7]=[C:6]([CH3:8])[CH:5]=[C:4]([CH3:9])[N:3]=1

Komponenten

7

Edukt 4

HCID 5234Sodium ChlorideHCID 14798Sodium HydroxideHCID 215072-Amino-4,6-dimethylpyridineHCID 23668193Sodium Nitrite

Produkt 1

HCID 125083782-Chloro-4,6-dimethylpyridineAusbeute 22 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 313Hydrochloric AcidLösungsmittelHCID 962WaterLösungsmittel2×

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

2-Amino-4,6-dimethyl-pyridine (4 g, 32.7 mmol) was dissolved in conc. hydrochloric acid (50 mL) and cooled to 0° C. A solution of sodium nitrite (3.39 g, 49.1 mmol) in water (20 mL) was added dropwise, followed by a solution of sodium chloride (3.8 g, 65 mmol) in water (20 mL). The mixture was stirred for 30 min. then basified with 20% sodium hydroxide solution and extracted with ethyl acetate. The combined extracts were washed with brine, dried over sodium sulfate and concentrated in vacuo to give a residue which was purified by column chromatography on silica gel (60-120 mesh) using 5% ethyl acetate/petroleum ether as eluent to afford 2-chloro-4,6-dimethyl-pyridine (1 g, 22%) as a solid.

Aufarbeitung

  1. extractionextracted with ethyl acetate
  2. washThe combined extracts were washed with brine
  3. dry with materialdried over sodium sulfate
  4. concentrationconcentrated in vacuo
  5. customto give a residue which
  6. customwas purified by column chromatography on silica gel (60-120 mesh)

Quellen und Nachweise

ORD-Eintrag
ord-43d0f9857d544775a93bc02b991ad1cf
Quelldatensatz
uspto-grants-2013_09
Patentnummer
US08524705B2

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