4-Aminopyridine → 4-(2,2,2-Trimethylacetamido)pyridine

HRID 34080

Reaktionsgleichung

Reaktionsgleichung von HRID 34080
[NH2:1][C:2]1[CH:7]=[CH:6][N:5]=[CH:4][CH:3]=1.[C:8](Cl)(=[O:13])[C:9]([CH3:12])([CH3:11])[CH3:10]>ClCCl.C(N(CC)CC)C>[CH3:10][C:9]([CH3:12])([CH3:11])[C:8]([NH:1][C:2]1[CH:7]=[CH:6][N:5]=[CH:4][CH:3]=1)=[O:13]

Komponenten

5

Edukt 2

HCID 17274-AminopyridineHCID 62493Pivaloyl chloride

Produkt 1

HCID 4270594-(2,2,2-Trimethylacetamido)pyridine

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6344DichloromethaneLösungsmittelHCID 8471TriethylamineLösungsmittel

Versuchsvorschrift

To a solution of 20.0 g of 4-aminopyridine in 100 mL of dichloromethane, 32.6 mL of triethylamine was added at 0° C., followed by 27.5 mL of pivaloyl chloride, and stirred at this temperature for 1 hour. The organic layer was washed successively with water and saturated brine, dried over anhydrous magnesium sulfate, and the solvent was evaporated, and the precipitated crystals were collected by filtration, and washed with a mixed solvent of diethyl ether and n-hexane. The filtrate was diluted with ethanol, and treated with 5 N sodium hydroxide at room temperature, thereby hydrolyzing coexisting dipivaloyl compounds into monopivaloyl compounds. Following neutralization with 5N hydrochloric acid, and extraction with ethyl acetate, the organic layer was washed with saturated brine, dried over anhydrous magnesium sulfate, and the solvent was evaporated, the precipitated crystals were collected by filtration, and washed with a mixed solvent of diethyl ether and n-hexane. This was then combined with the previously obtained crystals, to afford 25.1 g of the title compound as colorless crystals.

Aufarbeitung

  1. washThe organic layer was washed successively with water and saturated brine
  2. dry with materialdried over anhydrous magnesium sulfate
  3. customthe solvent was evaporated
  4. filtrationthe precipitated crystals were collected by filtration
  5. washwashed with a mixed solvent of diethyl ether and n-hexane
  6. additionThe filtrate was diluted with ethanol
  7. additiontreated with 5 N sodium hydroxide at room temperature
  8. extractionwith 5N hydrochloric acid, and extraction with ethyl acetate
  9. washthe organic layer was washed with saturated brine
  10. dry with materialdried over anhydrous magnesium sulfate
  11. customthe solvent was evaporated
  12. filtrationthe precipitated crystals were collected by filtration
  13. washwashed with a mixed solvent of diethyl ether and n-hexane

Quellen und Nachweise

ORD-Eintrag
ord-c494546c714c4b5694baa78639d6dd41
Quelldatensatz
uspto-grants-2008_09
Patentnummer
US07429609B2

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