Sodium Hydroxide → 4-(5-Hydroxypyridin-3-yl)benzonitrile

HRID 1685404Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1685404
C[O:2][C:3]1[CH:4]=[C:5]([C:9]2[CH:16]=[CH:15][C:12]([C:13]#[N:14])=[CH:11][CH:10]=2)[CH:6]=[N:7][CH:8]=1.Cl.[NH+]1C=CC=CC=1.[OH-].[Na+]>O>[OH:2][C:3]1[CH:4]=[C:5]([C:9]2[CH:16]=[CH:15][C:12]([C:13]#[N:14])=[CH:11][CH:10]=2)[CH:6]=[N:7][CH:8]=1

Komponenten

5

Edukt 3

HCID 14798Sodium HydroxideHCID 21584435Pyridinium hydrochlorideHCID 672914774-(5-Methoxy-3-pyridinyl)benzonitrile

Produkt 1

HCID 532175154-(5-Hydroxypyridin-3-yl)benzonitrileAusbeute 76 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 962WaterLösungsmittel

Reaktionsbedingungen

Temperatur
160 °C

Versuchsvorschrift

A mixture of 1.9 g (9.02 mM) of 4-(5-methoxy-3-pyridinyl)benzonitrile and 6.39 g (54.2 mM) of pyridinium hydrochloride is heated at 160° C. for 5 hours. After cooling and the addition of water, the pH is adjusted to 5 with concentrated sodium hydroxide solution. The mixture is extracted with ethyl acetate and the extract is dried over magnesium sulfate and concentrated under reduced pressure. The evaporation residue is purified by chromatography on a silica column (eluent: dichloromethane/ethyl acetate 92/8; v/v, then dichloromethane/methanol 9/1; v/v) to give the expected product in the form of a beige solid with a yield of 76%.

Aufarbeitung

  1. temperatureAfter cooling
  2. extractionThe mixture is extracted with ethyl acetate
  3. dry with materialthe extract is dried over magnesium sulfate
  4. concentrationconcentrated under reduced pressure
  5. customThe evaporation residue is purified by chromatography on a silica column (eluent

Quellen und Nachweise

ORD-Eintrag
ord-87ed16d436274bd0ae60be52cb000c08
Quelldatensatz
uspto-grants-2012_04
Patentnummer
US08148407B2

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