Hydrochloric Acid → 5-Chloro-6-ethyl-nicotinic acid

HRID 900970

Reaktionsgleichung

Reaktionsgleichung von HRID 900970
[Cl:1][C:2]1[C:3](Cl)=[N:4][CH:5]=[C:6]([CH:10]=1)[C:7]([OH:9])=[O:8].[CH2:12]([Mg]Cl)[CH3:13].Cl>C1COCC1.Cl[Ni]Cl.C1(P(C2C=CC=CC=2)CCP(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>[Cl:1][C:2]1[C:3]([CH2:12][CH3:13])=[N:4][CH:5]=[C:6]([CH:10]=1)[C:7]([OH:9])=[O:8]

Komponenten

6

Edukt 3

HCID 313Hydrochloric AcidHCID 2479875,6-Dichloronicotinic acidHCID 178461633HCID 178461633, Verbindung

Produkt 1

HCID 691547535-Chloro-6-ethyl-nicotinic acid

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 2734542[1,2-Bis(diphenylphosphino)ethane]dichloronickel(II)KatalysatorHCID 8028TetrahydrofuranLösungsmittel

Reaktionsbedingungen

Temperatur
55 °C

Versuchsvorschrift

To solution of 5,6-dichloronicotinic acid (21.46 g, 112 mmol) and 1,2-bis(diphenylphosphino)ethane dichloronickel(II) ((Ni(dppe)Cl2) (2.00 g, 3.6 mmol) in THF (60 mL, 1.9 M) is cooled to 0° C. and treated with ethyl magnesium chloride (2.8 M, 107 mL, 300 mmol) slowly via syringe with stirring under nitrogen. The reaction mixture is warmed to 55° C. for 3 h, cooled to 0° C. and acidified to pH 5 with 2 M HCl (100 mL). After concentrating in vacuo, the solution is reconstituted and extracted with ethyl acetate (2×200 mL), dried over Na2SO4, filtered and concentrated. The solvent removed in vacuo to provide crude 5-chloro-6-ethyl-nicotinic acid as a light brown glass (ESI-LCMS m/z calcd for C8H8ClNO2: 185.0; found 186.0 (M+1)+, which is used without further purification.

Aufarbeitung

  1. temperaturecooled to 0° C.
  2. concentrationAfter concentrating in vacuo
  3. extractionextracted with ethyl acetate (2×200 mL)
  4. dry with materialdried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customThe solvent removed in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-a8e1b3e4b3764c4ca6f7f180172e97d4
Quelldatensatz
uspto-grants-2008_04
Patentnummer
US07361671B2

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