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

HRID 59594

반응식

HRID 59594 반응식
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]>O.Cl[Ni]Cl.[Zn]>[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

참가 물질

6

반응물 2

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

생성물 1

HCID 129936922-Pyridinecarboxylic acid, 4,5,6-trichloro-수율 33.7%

시약·촉매·용매 3

HCID 23994Zinc촉매HCID 24385Nickel Dichloride촉매HCID 962Water용매

실험 절차

A 25 mL scintillation vial was charged with NiCl2 (76.2 mg, 0.586 mmol) and 2,2′-bipyridine (188.4 mg, 1.20 mmol). The vial was sealed and purged with nitrogen for 20 min. The inert reactor was charged with DMF (9 mL) and water (1 mL). The resulting mixture was allowed to stir for 24 h, and then solid 3,4,5,6-tetrachloropicolinic acid (1.54 g, 5.9 mmol) and zinc powder (3.33 g, 50.9 mmol) were added through the top of the reactor. The reaction mixture was allowed to stir at ambient temperature for 3 h and was diluted to 20 mL with water. The resulting heterogeneous mixture was filtered to remove the solids, and the resulting clear, aqueous filtrate was made acidic (pH˜1) with concentrated HCl. Upon standing, a fine white solid formed and was collected via vacuum filtration to give the title compound (0.45 g, 33.6%) that was 86% pure as analyzed by calibrated HPLC. The residual material was 9% unreacted starting material and 2 unknown impurities.

후처리

  1. customThe vial was sealed
  2. custompurged with nitrogen for 20 min
  3. additionThe inert reactor was charged with DMF (9 mL) and water (1 mL)
  4. stirringto stir at ambient temperature for 3 h
  5. filtrationThe resulting heterogeneous mixture was filtered
  6. customto remove the solids
  7. customa fine white solid formed
  8. filtrationwas collected via vacuum filtration

출처 및 근거

ORD 기록
ord-9466a4db791d4a16a297a28b70e01dd2
출처 데이터셋
uspto-grants-2016_09
특허 번호
US09440923B2

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