2-Chloropyridine → Picolinic acid

HRID 1266628Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1266628
[C:1](=[O:4])([O-])[O-:2].[Na+].[Na+].Cl[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][N:9]=1.C12(PC34CC(CC3)CC4)CC(CC1)CC2>C(O)C.O.C(Cl)Cl.[Cl-].[Cl-].C(#N)C1C=CC=CC=1.C(#N)C1C=CC=CC=1.[Pd+2]>[N:9]1[CH:10]=[CH:11][CH:12]=[CH:13][C:8]=1[C:1]([OH:2])=[O:4]

Komponenten

8

Edukt 3

HCID 79772-ChloropyridineHCID 10340Sodium CarbonateHCID 22679109HCID 22679109, Verbindung

Produkt 1

HCID 1018Picolinic acid

Reagenzien, Katalysatoren, Lösungsmittel 4

HCID 10271322Benzonitrile;dichloropalladiumKatalysatorHCID 702EthanolLösungsmittel2×HCID 962WaterLösungsmittelHCID 6344DichloromethaneLösungsmittel

Reaktionsbedingungen

Temperatur
100 °C

Versuchsvorschrift

Sodium carbonate (3.34 g, 32 mmols), 2-chloropyridine (2.38 g, 21 mmols) and 40 ml of ethanol are placed in a glass autoclave. The autoclave is rinsed with nitrogen and heated to 100° C. A solution of palladium bis(benzonitrile) dichloride (161 mg, 0.42 mmols) and dinorbornylphosphine (420 mg, 1.90 mmols) in 2 ml of ethanol (prepared under argon) is added, and then 5 bars CO are applied. After 16 hours at 120° C., the mixture is allowed to cool. The reaction mixture is taken up in water and methylene chloride. The aqueous phase is separated, acidified with concentrated hydrochloric acid and concentrated. The residue is extracted with ethanol and, after filtration, the ethanol is distilled off in a vacuum. The solid is recrystallised from water/ethanol/acetone. Yield of title compound as the hydrochloride: 2.13 g (64%).

Aufarbeitung

  1. washThe autoclave is rinsed with nitrogen
  2. temperatureto cool
  3. customThe aqueous phase is separated
  4. concentrationconcentrated
  5. extractionThe residue is extracted with ethanol
  6. filtrationafter filtration
  7. distillationthe ethanol is distilled off in a vacuum
  8. customThe solid is recrystallised from water/ethanol/acetone

Quellen und Nachweise

ORD-Eintrag
ord-796e4c62a0e44f13b50f791c0de1c113
Quelldatensatz
uspto-grants-2003_04
Patentnummer
US06548684B2

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