Hydrochloric Acid → Ethyl 7-chloroimidazo[1,2-A]pyridine-3-carboxylate

HRID 706545Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 706545
Cl[C:2]([C:5]([O:7][CH2:8][CH3:9])=[O:6])=[CH:3][O-].[K+].Cl.[Cl:12][C:13]1[CH:18]=[CH:17][N:16]=[C:15]([NH2:19])[CH:14]=1.C(=O)([O-])[O-].[Na+].[Na+]>CCO.O>[Cl:12][C:13]1[CH:18]=[CH:17][N:16]2[C:2]([C:5]([O:7][CH2:8][CH3:9])=[O:6])=[CH:3][N:19]=[C:15]2[CH:14]=1

Komponenten

7

Edukt 4

HCID 313Hydrochloric Acid2×HCID 10340Sodium CarbonateHCID 5818662-Amino-4-chloropyridineHCID 74089075Potassium 2-chloro-3-ethoxy-3-oxoprop-1-en-1-olate2×

Produkt 1

HCID 67107280Ethyl 7-chloroimidazo[1,2-A]pyridine-3-carboxylateAusbeute 88,7 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 702EthanolLösungsmittel2×HCID 962WaterLösungsmittel

Reaktionsbedingungen

Temperatur
70 °C

Versuchsvorschrift

To a flask equipped with a reflux condenser, mechanical stirring, and internal temperature probe was added potassium 2-chloro-3-ethoxy-3-oxoprop-1-en-1-olate (58.70 g, 311.1 mmol) followed by 200 mL of EtOH. Aqueous hydrogen chloride (4.862 ml, 15.56 mmol) in EtOH was added to the slurry. The slurry was stirred for about 15 minutes, and then 4-chloropyridin-2-amine (20.00 g, 155.6 mmol) was added, and the mixture was warmed to 70° C. After about one hour, an additional 2 equivalents of 3.2 M aqueous HCl were added and the mixture stirred at 70° C. for 16 hours. An additional 30 g of potassium 2-chloro-3-ethoxy-3-oxoprop-1-en-1-olate were added and the mixture was stirred at 70° C. for 2 hours. The mixture was cooled to ambient temperature and 500 mL of water added, followed by pH adjustment to 11 with 10% aqueous sodium carbonate. After stirring for several hours, the precipitated solids were collected by filtration and dried under vacuum to give 31 g (88%) of the title compound.

Aufarbeitung

  1. customTo a flask equipped with a reflux condenser
  2. waitAfter about one hour
  3. stirringthe mixture stirred at 70° C. for 16 hours
  4. stirringthe mixture was stirred at 70° C. for 2 hours
  5. temperatureThe mixture was cooled to ambient temperature
  6. stirringAfter stirring for several hours
  7. filtrationthe precipitated solids were collected by filtration
  8. customdried under vacuum

Quellen und Nachweise

ORD-Eintrag
ord-3171bad0ce704fdebb9e93cc2d8752b6
Quelldatensatz
uspto-grants-2015_11
Patentnummer
US09174981B2

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