Pyridine → 2-Chloro-5-methyl-3-nitropyridine

HRID 72644

Reaktionsgleichung

Reaktionsgleichung von HRID 72644
[CH3:1][C:2]1[CH:3]=[C:4]([N+:9]([O-:11])=[O:10])[C:5](=O)[NH:6][CH:7]=1.N1C=CC=CC=1.P(Cl)(Cl)([Cl:20])=O.C(=O)([O-])[O-].[Na+].[Na+]>ClC1C=CC=CC=1>[Cl:20][C:5]1[C:4]([N+:9]([O-:11])=[O:10])=[CH:3][C:2]([CH3:1])=[CH:7][N:6]=1

Komponenten

6

Edukt 4

HCID 1049PyridineHCID 10340Sodium CarbonateHCID 24813Phosphorus oxychlorideHCID 3456432-Hydroxy-5-methyl-3-nitropyridine

Produkt 1

HCID 8183002-Chloro-5-methyl-3-nitropyridineAusbeute 75,3 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 7964ChlorobenzeneLösungsmittel

Versuchsvorschrift

A solution of 5-methyl-3-nitro-1H-pyridone (3.1 g, 20 mmol) in 50 mL chlorobenzene was treated with pyridine (0.47 g, 6.0 mmol) and phosphorus oxychloride (4.7 g, 30.8 mmol). The mixture was refluxed for 1 h. Upon cooling it was treated with sodium carbonate aq. followed by extraction with CH2Cl2. The organic phase was dried over Mg2SO4 and filtered. The solvent was evaporated in vacuo to give 2.6 g of the titled compound which was further purified by flash chromatography on silica gel (PE:EtOAc, 8:2, v/v). 1H-NMR (CDCl3) δ: 2.45 (s, 3H, CH3), 8.44 (d, 1H, J=2.0 Hz, Py-H), 8.58 (d, 1H, J=2.0 Hz, Py-H); MS (ESI+) m/z 173.0209 [M+H]+, C6H5ClN2O2 requires 172.0040.

Aufarbeitung

  1. temperatureThe mixture was refluxed for 1 h
  2. temperatureUpon cooling it
  3. extractionfollowed by extraction with CH2Cl2
  4. dry with materialThe organic phase was dried over Mg2SO4
  5. filtrationfiltered
  6. customThe solvent was evaporated in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-bc06ef7e8e45493bbceced2dbb99d141
Quelldatensatz
uspto-grants-2014_09
Patentnummer
US08829003B2

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