Phosphorus oxychloride → 3-Chloropyridine-4-carbonitrile

HRID 487301

Reaktionsgleichung

Reaktionsgleichung von HRID 487301
[C:1]([C:3]1[CH:8]=[CH:7][N+:6]([O-])=[CH:5][CH:4]=1)#[N:2].P(Cl)(Cl)([Cl:12])=O.P(Cl)(Cl)(Cl)(Cl)[Cl:16]>>[Cl:12][C:7]1[CH:8]=[C:3]([C:1]#[N:2])[CH:4]=[CH:5][N:6]=1.[Cl:16][C:4]1[CH:5]=[N:6][CH:7]=[CH:8][C:3]=1[C:1]#[N:2]

Komponenten

5

Edukt 3

HCID 24813Phosphorus oxychlorideHCID 24819Phosphorus pentachlorideHCID 846844-Pyridinecarbonitrile, 1-oxide

Produkt 2

HCID 5686382-Chloro-4-cyanopyridineAusbeute 24 %HCID 106783063-Chloropyridine-4-carbonitrileAusbeute 30 %

Versuchsvorschrift

A mixture of 4-cyanopyridine N-oxide (30 g, 0.25 mol), phosphorous oxychloride (96 ml, 0.35 mol) and phosphorous pentachloride (72 g, 0.38 mol) was refluxed at 120°-130° C. for 6 hours and then stirred at room temperature for 12 hours. The reaction mixture was slowly poured into a mixture of ice/Na2CO3 /K2CO3 and was extracted with chloroform (4×250 ml). The solvent was removed in vacuo and the residue was purified by column chromatography on silica eluting with 50% ether/hexanes to afford 8.4 g (24%) of 2-chloro-4-cyanopyridine, m.p. 69.5°-70.5° C. and 10.5 g (30%) of 3-chloro-4-cyanopyridine, m.p. 71.5°-72° C.

Aufarbeitung

  1. temperaturewas refluxed at 120°-130° C. for 6 hours
  2. extractionwas extracted with chloroform (4×250 ml)
  3. customThe solvent was removed in vacuo
  4. customthe residue was purified by column chromatography on silica eluting with 50% ether/hexanes

Quellen und Nachweise

ORD-Eintrag
ord-ae7c8d4b49f24e46820621d7ec7f4434
Quelldatensatz
uspto-grants-1994_03
Patentnummer
US05294612

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