Hydrochloric Acid → 5-(Chloromethyl)pyridine-3-carbonitrile

HRID 45239Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 45239
O[CH2:2][C:3]1[CH:4]=[C:5]([C:9]#[N:10])[CH:6]=[N:7][CH:8]=1.Cl.S(Cl)([Cl:14])=O>C(Cl)Cl.O1CCOCC1.C1(C)C=CC=CC=1>[Cl:14][CH2:2][C:3]1[CH:4]=[C:5]([C:9]#[N:10])[CH:6]=[N:7][CH:8]=1

Komponenten

7

Edukt 3

HCID 313Hydrochloric AcidHCID 24386Thionyl ChlorideHCID 224165405-(Hydroxymethyl)nicotinonitrile

Produkt 1

HCID 221467115-(Chloromethyl)pyridine-3-carbonitrileAusbeute 73 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 1140TolueneLösungsmittelHCID 6344DichloromethaneLösungsmittelHCID 312751,4-DioxaneLösungsmittel

Reaktionsbedingungen

Temperatur
60 °C

Versuchsvorschrift

To 0.2 g (1.49 mmol) of 5-(hydroxymethyl)pyridine-3-carbonitrile in 2 mL of DCM is added 1 mL (4 mmol) of HCl 4N in dioxane. The mixture is concentrated under reduced pressure and then added to 0.65 mL (8.95 mmol) of thionyl chloride followed by heating for 3 hours at 60° C. After cooling to room temperature, the medium is taken up in 20 mL of toluene, and the precipitate formed is filtered off and then treated with 30 mL of DCM and 30 mL of saturated NaHCO3 solution. The organic phase is separated out and dried over Na2SO4 and then concentrated under reduced pressure. 161 mg of 5-(chloromethyl)pyridine-3-carbonitrile are obtained in the form of an oil.

Aufarbeitung

  1. concentrationThe mixture is concentrated under reduced pressure
  2. temperatureAfter cooling to room temperature
  3. customthe precipitate formed
  4. filtrationis filtered off
  5. additiontreated with 30 mL of DCM and 30 mL of saturated NaHCO3 solution
  6. customThe organic phase is separated out
  7. dry with materialdried over Na2SO4
  8. concentrationconcentrated under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-37f5b4211c5b44b7a55b815ae1fc5d17
Quelldatensatz
uspto-grants-2013_09
Patentnummer
US08541455B2

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