2-Chloronicotinic acid → 2-Ethoxypyridine-3-carboxylic acid

HRID 393899Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 393899
[CH3:1][C:2](C)([O-:4])C.[K+].Cl[C:8]1[N:16]=[CH:15][CH:14]=[CH:13][C:9]=1[C:10]([OH:12])=[O:11]>C(O)C>[CH2:2]([O:4][C:8]1[N:16]=[CH:15][CH:14]=[CH:13][C:9]=1[C:10]([OH:12])=[O:11])[CH3:1]

Komponenten

4

Edukt 2

HCID 762582-Chloronicotinic acidHCID 23665647Potassium tert-butoxide

Produkt 1

HCID 27363452-Ethoxypyridine-3-carboxylic acidAusbeute 8,6 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 702EthanolLösungsmittel2×

Reaktionsbedingungen

Temperatur
170 °C

Versuchsvorschrift

A solution of potassium t-butoxide (44.9 g, 0.40 mol) in absolute ethanol (300 mL) was added slowly to a solution of 2-chloronicotinic acid (30 g, 0.19 mol) in ethanol (100 mL), and the reaction heated in a sealed vessel at 170° C. for 20 h. On cooling, the reaction mixture was concentrated under reduced pressure, the residue dissolved in water (200 mL) and acidified to pH 3 with aqueous hydrochloric acid. The aqueous solution was extracted with dichloromethane (4×200 mL), the organic phases combined, dried (Na2SO4) and concentrated under reduced pressure to afford the title compound (27.4 g, 16.4 mmol) as a white solid.

Aufarbeitung

  1. temperatureOn cooling
  2. concentrationthe reaction mixture was concentrated under reduced pressure
  3. dissolutionthe residue dissolved in water (200 mL)
  4. extractionThe aqueous solution was extracted with dichloromethane (4×200 mL)
  5. dry with materialdried (Na2SO4)
  6. concentrationconcentrated under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-cfa2be1a1a9d4c82b3940ab982d1b055
Quelldatensatz
uspto-grants-2004_10
Patentnummer
US06809200B2

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