Reaktion #87871

Reaktionsgleichung

2,2′-bipyridine

3,4,5,6-tetrachloropicolinic acid

→

title compound

Ausbeute 35.9%

4,5,6-trichloropicolinic Acid

Ausbeute 35.9%

Lösungsmittel

water

Reaktionsbedingungen

Aufarbeitung

1. 1
   SonstigeThe solids were removed by filtration
2. 2
   Waschenwashed with water (100 mL)
3. 3
   SonstigeThe solid was isolated
4. 4
   Waschenwashed with water
5. 5
   Sonstigedried under vacuum

Vorschrift

Anhydrous nickel chloride (NiCl2; 77 milligrams (mg), 0.596 millimoles (mmol)) and 2,2′-bipyridine (186 mg, 1.19 mmol) were stirred in 9:1 dimethylformamide (DMF)-water (10 milliliters (mL)) for 24 hours (h). Solid 3,4,5,6-tetrachloropicolinic acid (1.556 grams (g), 5.96 mmol) was added, followed by zinc powder (3.32 g, 50.7 mmol). After 3 h, water was added. The solids were removed by filtration and washed with water (100 mL). The aqueous filtrate was made acidic (pH 1) with concentrated hydrochloric acid (HCl). A white solid appeared upon standing. The solid was isolated, washed with water and dried under vacuum to give the title compound (484 mg, 35.8%) which was 94% pure by high-performance liquid chromatography (HPLC): 1H NMR (400 MHz, DMSO-d6) δ 8.21 (s, 1H); 13C NMR (101 MHz, DMSO-d6) δ 163.4, 148.9, 146.5, 144.4, 131.6, 125.7.

Quelle