Phosphorus oxychloride → Ethyl 2-chloro-5-cyano-6-methylnicotinate

HRID 27754

Reaktionsgleichung

Reaktionsgleichung von HRID 27754
[C:1]([C:3]1[CH:4]=[C:5]([C:11]([O:13][CH2:14][CH3:15])=[O:12])[C:6](O)=[N:7][C:8]=1[CH3:9])#[N:2].P(Cl)(Cl)([Cl:18])=O>>[Cl:18][C:6]1[C:5]([C:11]([O:13][CH2:14][CH3:15])=[O:12])=[CH:4][C:3]([C:1]#[N:2])=[C:8]([CH3:9])[N:7]=1

Komponenten

3

Edukt 2

HCID 24813Phosphorus oxychlorideHCID 178469023HCID 178469023, Verbindung

Produkt 1

HCID 2758816Ethyl 2-chloro-5-cyano-6-methylnicotinate

Versuchsvorschrift

200 g of 5-cyano-2-hydroxy-6-methyl-3-pyridine-carboxylic acid, ethyl ester (1 mol) are refluxed with stirring in 750 ml of phosphorous oxychloride for 5 hours. The excess of phosphorous oxychloride is removed in vacuo and the residue poured in 1 kg of ice. 2-chloro-5-cyano-6-methyl-3-pyridine-carboxylic acid, ethyl ester crystallizes and is filtered off. Yield 170 g (76%); m.p. 43°-45° C. (petrol ether).

Aufarbeitung

  1. customThe excess of phosphorous oxychloride is removed in vacuo
  2. additionthe residue poured in 1 kg of ice
  3. custom2-chloro-5-cyano-6-methyl-3-pyridine-carboxylic acid, ethyl ester crystallizes
  4. filtrationis filtered off

Quellen und Nachweise

ORD-Eintrag
ord-7bb211f2fe674db5b482addbf408b649
Quelldatensatz
uspto-grants-1980_09
Patentnummer
US04223142

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