2,2'-Bipyridine → 2-Pyridinecarboxylic acid, 4,5,6-trichloro-

HRID 59593

Reaktionsgleichung

Reaktionsgleichung von HRID 59593
N1C=CC=CC=1C1C=CC=CN=1.Cl[C:14]1[C:15]([C:23]([OH:25])=[O:24])=[N:16][C:17]([Cl:22])=[C:18]([Cl:21])[C:19]=1[Cl:20]>[Ni](Cl)Cl.[Zn].O>[Cl:20][C:19]1[C:18]([Cl:21])=[C:17]([Cl:22])[N:16]=[C:15]([C:23]([OH:25])=[O:24])[CH:14]=1

Komponenten

6

Edukt 2

HCID 14742,2'-BipyridineHCID 826463,4,5,6-Tetrachloropyridine-2-carboxylic acid

Produkt 1

HCID 129936922-Pyridinecarboxylic acid, 4,5,6-trichloro-Ausbeute 35,9 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 23994ZincKatalysatorHCID 24385Nickel DichlorideKatalysatorHCID 962WaterLösungsmittel

Versuchsvorschrift

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.

Aufarbeitung

  1. customThe solids were removed by filtration
  2. washwashed with water (100 mL)
  3. customThe solid was isolated
  4. washwashed with water
  5. customdried under vacuum

Quellen und Nachweise

ORD-Eintrag
ord-4e5751f64c2b41a483cdbb265a523c27
Quelldatensatz
uspto-grants-2016_09
Patentnummer
US09440923B2

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