Phosphorus oxychloride → 6-Chloro-4-methylpyridine-3-carboxylic acid

HRID 968109Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 968109
O[C:2]1[CH:10]=[C:9]([CH3:11])[C:5]([C:6]([OH:8])=[O:7])=[CH:4][N:3]=1.P(Cl)(Cl)([Cl:14])=O>O>[CH3:11][C:9]1[C:5]([C:6]([OH:8])=[O:7])=[CH:4][N:3]=[C:2]([Cl:14])[CH:10]=1

Komponenten

4

Edukt 2

HCID 24813Phosphorus oxychlorideHCID 178429282HCID 178429282, Verbindung

Produkt 1

HCID 222917476-Chloro-4-methylpyridine-3-carboxylic acidAusbeute 81 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 962WaterLösungsmittel

Versuchsvorschrift

6-Hydroxy-4-methylnicotinic acid (10 g, 65.3 mmol) and phosphorus oxychloride (33 mL) were combined and refluxed for 3 hours. The reaction solution was poured into 300 mL of ice and then 600 mL of water was added. The solution was boiled for 30 minutes before cooling and extracting the product into ether. The solvent was removed and the residue was recrystallized from 900 mL of hot water. Yellow solid, 9.06 g (81% yield). Mp 170-172° C. 1H NMR (CD3OD): δ 2.61 (s, 3H), 7.41 (s, 1H), 8.80 (s, 1H). LC-MS, M+1=172.

Aufarbeitung

  1. temperaturerefluxed for 3 hours
  2. temperaturebefore cooling
  3. extractionextracting the product into ether
  4. customThe solvent was removed
  5. customthe residue was recrystallized from 900 mL of hot water

Quellen und Nachweise

ORD-Eintrag
ord-c7eb2b1e3d384d57a246edba14086373
Quelldatensatz
uspto-grants-2005_10
Patentnummer
US06956052B2

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