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

HRID 59593

反応式

HRID 59593 の反応式
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

参加物

6

反応物 2

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

生成物 1

HCID 129936922-Pyridinecarboxylic acid, 4,5,6-trichloro-収率 35.9%

試薬・触媒・溶媒 3

HCID 23994Zinc触媒HCID 24385Nickel Dichloride触媒HCID 962Water溶媒

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-4e5751f64c2b41a483cdbb265a523c27
出典データセット
uspto-grants-2016_09
特許番号
US09440923B2

関連ノート

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