Hydrochloric Acid → 4,6-Dichloronicotinic acid

HRID 494695Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 494695
[OH-].[Na+].C([O:5][C:6](=[O:15])[C:7]1[C:12]([Cl:13])=[CH:11][C:10]([Cl:14])=[N:9][CH:8]=1)C.C1COCC1.CO.O.Cl>CCOC(C)=O.CCOCC>[Cl:13][C:12]1[C:7]([C:6]([OH:15])=[O:5])=[CH:8][N:9]=[C:10]([Cl:14])[CH:11]=1

Komponenten

6

Edukt 4

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 600045Ethyl 4,6-dichloropyridine-3-carboxylateHCID 21892291Methanol tetrahydrofuran water

Produkt 1

HCID 8171584,6-Dichloronicotinic acidAusbeute 96 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 21584169Diethylether ethylacetateLösungsmittel

Versuchsvorschrift

Sodium hydroxide (40 mL, 6.25 M solution) was added to a stirred solution of 4,6-dichloronicotinic acid ethyl ester (22) (25.95 g, 118 mmol) in 4:1:1 THF/MeOH/water (600 mL). After 30 minutes, the reaction mixture was acidified to pH 2 with concentrated HCl, diluted with 1:1 EtOAc/Et2O and washed with water and brine. The organic layer was dried (Na2SO4) and concentrated. The resulting off-white solid was twice concentrated from toluene to give the desired product (23) as a white solid (21.73 g, 96%).

Aufarbeitung

  1. washwashed with water and brine
  2. dry with materialThe organic layer was dried (Na2SO4)
  3. concentrationconcentrated
  4. concentrationThe resulting off-white solid was twice concentrated from toluene

Quellen und Nachweise

ORD-Eintrag
ord-1748d4f12e074797b231a6b3dc98d26d
Quelldatensatz
uspto-grants-2009_05
Patentnummer
US07538120B2

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