Potassium Iodide → 2-Amino-5-fluoro-3-iodopyridine

HRID 60218

Reaktionsgleichung

Reaktionsgleichung von HRID 60218
[F:1][C:2]1[CH:3]=[CH:4][C:5]([NH2:8])=[N:6][CH:7]=1.[I:9]([O-])(=O)=O.[K+].[I-].[K+]>S(=O)(=O)(O)O.O>[F:1][C:2]1[CH:3]=[C:4]([I:9])[C:5]([NH2:8])=[N:6][CH:7]=1

Komponenten

6

Edukt 3

HCID 4875Potassium IodideHCID 27377012-Amino-5-fluoropyridineHCID 23665710Potassium Iodate

Produkt 1

HCID 184559742-Amino-5-fluoro-3-iodopyridineAusbeute 116,9 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 1118Sulfuric AcidLösungsmittel

Reaktionsbedingungen

Temperatur
100 °C

Versuchsvorschrift

A stirred solution of 5-fluoro-pyridin-2-ylamine (50 g, 0.45 mol) in 2M sulfuric acid (250 mL) was treated portionwise with potassium iodate (48 g, 0.22 mol) and the mixture heated to 100° C. A solution of potassium iodide (41 g, 0.24 mol) in water (100 mL) was added dropwise over ca. 1 hour. The mixture was allowed to stir for a further 30 minutes then cooled to ambient temperature. The pH of the aqueous phase was adjusted to 8-9 and the mixture extracted with ethyl acetate (×3). The combined organic layer was washed with aqueous sodium thiosulfate solution, water and brine, dried (Na2SO4), filtered and evaporated to afford the title compound as a yellow solid (61.2 g, 58%). 1H NMR (400 MHz, CDCl3): 7.94 (d, J=2.7 Hz, 1H), 7.68 (dd, J=7.2, 2.7 Hz, 1H), 4.85 (s, 2H).

Aufarbeitung

  1. temperaturethen cooled to ambient temperature
  2. extractionthe mixture extracted with ethyl acetate (×3)
  3. washThe combined organic layer was washed with aqueous sodium thiosulfate solution, water and brine
  4. dry with materialdried (Na2SO4)
  5. filtrationfiltered
  6. customevaporated

Quellen und Nachweise

ORD-Eintrag
ord-ee5df0ba6ae1490c9a8d79ee19b04bd0
Quelldatensatz
uspto-grants-2016_09
Patentnummer
US09440976B2

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