Isopropanol → Isopropyl 6-chloronicotinate

HRID 353825Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 353825
[C:1]([C:8]1NC=CN=1)([C:3]1NC=CN=1)=O.[Cl:13][C:14]1[CH:22]=[CH:21][C:17]([C:18]([OH:20])=[O:19])=[CH:16][N:15]=1.C(O)(C)C>ClCCl>[Cl:13][C:14]1[CH:22]=[CH:21][C:17]([C:18]([O:20][CH:1]([CH3:8])[CH3:3])=[O:19])=[CH:16][N:15]=1

Komponenten

5

Edukt 3

HCID 3776IsopropanolHCID 792226-Chloronicotinic acidHCID 5250894Bis-(1H-imidazol-2-YL)-methanone

Produkt 1

HCID 23512700Isopropyl 6-chloronicotinateAusbeute 114 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

Carbonyl diimidazole (18.6 g, 0.115 mol) was added to a suspension of 6-chloronicotinic acid (16.6 g, 0.105 mol) in dichloromethane (250 mL). After all of the solid had dissolved the reaction solution was stirred at ambient temperature for 1 hour and then isopropyl alcohol (100 mL) was added. The dichloromethane was removed under vacuum. A catalytic amount of sodium isopropoxide was added to the solution and the solution was heated at reflux for 1 hour. The solution was then concentrated under vacuum. The resulting residue was slurried with water and then extracted with diethyl ether. The extract was dried over magnesium sulfate and then concentrated under vacuum to provide 23.9 g of isopropyl 6-chloronicotinate.

Aufarbeitung

  1. dissolutionAfter all of the solid had dissolved the reaction solution
  2. customThe dichloromethane was removed under vacuum
  3. additionA catalytic amount of sodium isopropoxide was added to the solution
  4. temperaturethe solution was heated
  5. temperatureat reflux for 1 hour
  6. concentrationThe solution was then concentrated under vacuum
  7. extractionextracted with diethyl ether
  8. dry with materialThe extract was dried over magnesium sulfate
  9. concentrationconcentrated under vacuum

Quellen und Nachweise

ORD-Eintrag
ord-d6dfa5f61d3c4be9a8a85bd6da8e1945
Quelldatensatz
uspto-grants-2004_06
Patentnummer
US06756382B2

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