Reaktion #65770

Reaktionsgleichung

sodium hydrogencarbonate

2-amino-3,4-diethoxycarbonyl-5-nitro-6-phenylpyridine

hydrofluoroboric acid

sodium nitrite

→

3,4-Diethoxycarbonyl-2-fluoro-5-nitro-6-phenylpyridine

Lösungsmittel

water

acetic acid

Reaktionsbedingungen

Aufarbeitung

1. 1
   workup.ADDITIONwas added to the solution
2. 2
   SonstigeThirty minutes
3. 3
   Sonstigewas elevated to room temperature
4. 4
   Extraktionfollowed by extraction with ethyl acetate
5. 5
   WaschenAfter the organic layer was washed with water
6. 6
   Trocknena saturated aqueous solution of sodium chloride, and dried
7. 7
   workup.DISTILLATIONAfter the solvent was distilled off
8. 8
   Filtrationthe resulting crystals (2-pyridone compound) were collected by filtration with hexane
9. 9
   Waschenwashed
10. 10
    workup.DISTILLATIONThe solvent was distilled off from the obtained filtrate
11. 11
    Sonstigeto give an oily substance

Vorschrift

In 2 ml of acetic acid was dissolved 100 mg of 2-amino-3,4-diethoxycarbonyl-5-nitro-6-phenylpyridine, and 1.5 ml of 42% hydrofluoroboric acid was added to the solution. The mixture was cooled to -5° C., followed by adding dropwise a solution of 21 mg (1.1 eq) of sodium nitrite dissolved in 0.5 ml of water. Thirty minutes later, the temperature of the mixture was elevated to room temperature and the mixture was neutralized with sodium hydrogencarbonate, followed by extraction with ethyl acetate. After the organic layer was washed with water and a saturated aqueous solution of sodium chloride, and dried. After the solvent was distilled off, the resulting crystals (2-pyridone compound) were collected by filtration with hexane, and washed. The solvent was distilled off from the obtained filtrate, to give an oily substance.

Quelle