Hydrochloric Acid → Ethyl 2-(5-nitropyridin-2-YL)acetate

HRID 714866Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 714866
C([C:3]([C:14]1[CH:19]=[CH:18][C:17]([N+:20]([O-:22])=[O:21])=[CH:16][N:15]=1)(C([O-])=O)[C:4]([O:6][C:7](C)(C)[CH3:8])=[O:5])C.Cl>C(OCC)(=O)C>[CH2:7]([O:6][C:4](=[O:5])[CH2:3][C:14]1[CH:19]=[CH:18][C:17]([N+:20]([O-:22])=[O:21])=[CH:16][N:15]=1)[CH3:8]

Komponenten

4

Edukt 2

HCID 313Hydrochloric AcidHCID 67270067Tert-butyl ethyl(5-nitropyridin-2-yl)malonate

Produkt 1

HCID 18670679Ethyl 2-(5-nitropyridin-2-YL)acetateAusbeute 82,4 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

To tert-butyl ethyl(5-nitropyridin-2-yl)malonate (10 g) obtained in Step A of Example 153 was added a solution of 4 M hydrogen chloride in ethyl acetate (40 mL), and the mixture was stirred overnight at room temperature. The solvent was evaporated under reduced pressure, and diethyl ether (150 mL) and saturated aqueous sodium hydrogen carbonate solution were added thereto. To the reaction mixture was added sodium hydrogen carbonate until bubble generation stopped, and the mixture was extracted with ethyl acetate. The obtained organic layer was washed with saturated brine, and dried over anhydrous magnesium sulfate, and the solvent was evaporated under reduced pressure. The residue was purified by silica gel column chromatography (hexane/ethyl acetate) to give the title compound (5.6 g).

Aufarbeitung

  1. customThe solvent was evaporated under reduced pressure, and diethyl ether (150 mL) and saturated aqueous sodium hydrogen carbonate solution
  2. additionwere added
  3. additionTo the reaction mixture was added sodium hydrogen carbonate
  4. customuntil bubble generation
  5. extractionthe mixture was extracted with ethyl acetate
  6. washThe obtained organic layer was washed with saturated brine
  7. dry with materialdried over anhydrous magnesium sulfate
  8. customthe solvent was evaporated under reduced pressure
  9. customThe residue was purified by silica gel column chromatography (hexane/ethyl acetate)

Quellen und Nachweise

ORD-Eintrag
ord-9cae02d932f8481a8a4f69e8e97b1f04
Quelldatensatz
uspto-grants-2015_11
Patentnummer
US09187453B2

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