Acetic Acid → 2-Fluoro-4-methylpyridin-3-amine

HRID 1450150

Reaktionsgleichung

Reaktionsgleichung von HRID 1450150
[F:1][C:2]1[C:7]([N+:8]([O-])=O)=[C:6]([CH3:11])[CH:5]=[CH:4][N:3]=1.C(O)(=O)C.[H][H]>C(OCC)(=O)C.[Pd]>[NH2:8][C:7]1[C:2]([F:1])=[N:3][CH:4]=[CH:5][C:6]=1[CH3:11]

Komponenten

6

Edukt 3

HCID 176Acetic AcidHCID 124081822-Fluoro-4-methyl-3-nitropyridineHCID 178418361HCID 178418361, Verbindung

Produkt 1

HCID 27631612-Fluoro-4-methylpyridin-3-amine

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 23938PalladiumKatalysatorHCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

To a solution of 10.1 g (65 mmol) of 2-fluoro-4-methyl-3-nitropyridine in 200 mL of ethyl acetate was added 25 g (0.40 mol) of acetic acid and 0.8 g of 5 percent palladium on carbon catalyst. This mixture was shaken under 50 psig (pounds per square inch gauge) (2400 kiloPascals) pressure of hydrogen for 18 hours, was filtered, and was concentrated by evaporation under reduced pressure to obtain an oil. This oil was partitioned between dilute aqueous sodium bicarbonate and ether. The organic phase was separated, dried over magnesium sulfate, and filtered. The filtrate was concentrated by evaporation under reduced pressure and the residue was purified by column chromatography to obtain 7.2 g (88 percent of theory) of the title compound as a colorless solid, melting at 63°-64° C. Nuclear Magnetic Resonance Spectrum (200 MHz (megaHertz), CDC13): 1H: 7.4 (d, 1H, J=5.0); 6.8 (d, 1H, J=5.0); 3.7 (br, 2H); 2.1 (s, 3H); 13C: 152.6 (d, J=229); 134.1 (d, J=8.6); 133.8 (d, J=14.5 ); 128.1 (d, J=27.1 ); 123.3, 16.4 (d, J=4.1).

Aufarbeitung

  1. filtrationwas filtered
  2. concentrationwas concentrated by evaporation under reduced pressure
  3. customto obtain an oil
  4. customThis oil was partitioned between dilute aqueous sodium bicarbonate and ether
  5. customThe organic phase was separated
  6. dry with materialdried over magnesium sulfate
  7. filtrationfiltered
  8. concentrationThe filtrate was concentrated by evaporation under reduced pressure
  9. customthe residue was purified by column chromatography

Quellen und Nachweise

ORD-Eintrag
ord-00fab2b7daec40aa8e2392ca05baa4b8
Quelldatensatz
uspto-grants-1997_02
Patentnummer
US05602075

Verknüpfte Notizen

Wird geladen…