Phosphorus oxychloride → 6-Chloro-5-methylpyridine-2-carboxylic acid

HRID 631997

Reaktionsgleichung

Reaktionsgleichung von HRID 631997
[CH3:1][C:2]1[CH:7]=[N+:6]([O-])[C:5]([C:9]([OH:11])=[O:10])=[CH:4][CH:3]=1.P(Cl)(Cl)([Cl:14])=O>>[Cl:14][C:7]1[N:6]=[C:5]([C:9]([OH:11])=[O:10])[CH:4]=[CH:3][C:2]=1[CH3:1]

Komponenten

3

Edukt 2

HCID 24813Phosphorus oxychlorideHCID 866747432-Pyridinecarboxylic acid, 5-methyl-, 1-oxide

Produkt 1

HCID 183244376-Chloro-5-methylpyridine-2-carboxylic acidAusbeute 84,3 %

Reaktionsbedingungen

Temperatur
105 °C

Versuchsvorschrift

5-Methyl-2-pyridinecarboxylic acid 1-oxide (0.9 g, 5.88 mmol) was added to phosphoryl trichloride (30 mL). The mixture was stirred at 105° C. for 3 h. After that the mixture was cooled to room temperature, added to ice water slowly and extracted with methylene chloride (4×30 mL). The organic layer was washed with brine (50 mL), dried over anhydrous sodium sulfate, and concentrated to give the crude product (0.85 g, 84.3%); MS (EI): m/e=172.0 [M+H]+.

Aufarbeitung

  1. temperatureAfter that the mixture was cooled to room temperature
  2. extractionextracted with methylene chloride (4×30 mL)
  3. washThe organic layer was washed with brine (50 mL)
  4. dry with materialdried over anhydrous sodium sulfate
  5. concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag
ord-6885729ea5b4408fa8d4ebafc673e9e4
Quelldatensatz
uspto-grants-2016_04
Patentnummer
US09321727B2

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