Hydrochloric Acid → HCID 66862536, Verbindung

HRID 253719

Reaktionsgleichung

Reaktionsgleichung von HRID 253719
[H-].[Na+].[C:3]([CH2:11][C:12]([O:14][CH3:15])=[O:13])(=[O:10])[C:4]1[CH:9]=[CH:8][CH:7]=[N:6][CH:5]=1.[CH2:16](Br)[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1.Cl>C1COCC1>[CH2:16]([C:5]1[N:6]=[CH:7][CH:8]=[CH:9][C:4]=1[C:3]([CH2:11][C:12]([O:14][CH3:15])=[O:13])=[O:10])[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1

Komponenten

6

Edukt 4

HCID 313Hydrochloric AcidHCID 7498Benzyl BromideHCID 24758Sodium hydrideHCID 1086453-Pyridinepropanoic acid, beta-oxo-, methyl ester

Produkt 1

HCID 66862536HCID 66862536, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

NaH (300 mg; 60%) is added to the solution of methyl nicotinoylacetate (896 mg, 5 mmol) in THF (15 mL) at 0° C. under argon atmosphere. The reaction mixture is stirred for 15 minutes at the temperature and benzyl bromide (0.36 mL) is added. The reaction mixture is heated at reflux overnight. The reaction mixture is poured into iced 1N HCl and extracted with EtOAc three times. The combined organic extract is washed with brine and dried over MgSO4. Concentration under reduced pressure gives the residue which is purified over column chromatography to afford methyl 2-benzyl-nicotinoylacetate intermediate (389 mg).

Aufarbeitung

  1. additionis added
  2. temperatureThe reaction mixture is heated
  3. temperatureat reflux overnight
  4. extractionextracted with EtOAc three times
  5. extractionThe combined organic extract
  6. washis washed with brine
  7. dry with materialdried over MgSO4
  8. concentrationConcentration under reduced pressure
  9. customgives the residue which
  10. customis purified over column chromatography

Quellen und Nachweise

ORD-Eintrag
ord-08ed4b93160a4ce5a72746e74e7ddb3c
Quelldatensatz
uspto-grants-2011_01
Patentnummer
US07872142B2

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