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

HRID 59599

Reaction equation

HRID 59599 reaction equation
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]>[Zn].C(#N)C>[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

Participants

5

Reactant 2

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

Product 1

HCID 129936922-Pyridinecarboxylic acid, 4,5,6-trichloro-

Reagents, catalysts & solvents 2

HCID 23994ZincCatalystHCID 6342AcetonitrileSolvent

Procedure

Three 8 mL scintillation vials were charged with NiCl2.6H2O (12.0 mg, 0.051 mmol) and 2,2′-bipyridine (16.0 mg, 0.102 mmol). The vials were closed and purged with nitrogen for 5 min, after which the vials were charged with DMF (4.5 mL) and one of the following: deionized (DI) water (pH=7), 10% HCl, or 10% sodium hydroxide (NaOH) (0.5 mL). The mixtures were allowed to stir for 5 min. To each of the vials was added zinc dust (0.22 g, 3.4 mmol), and the mixtures were allowed to stir under nitrogen for 35 min. Solid 3,4,5,6-tetrachloropicolinic acid (0.10 g, 0.4 mmol) was added to each through the top of the reactor. The reaction mixtures were allowed to stir at ambient temperature, and samples were removed periodically to determine reaction kinetics. The samples (˜0.01 mL of reaction mixture diluted to 1.5 mL with acetonitrile) were analyzed by a calibrated HPLC method.

Workup

  1. customThe vials were closed
  2. custompurged with nitrogen for 5 min
  3. additionafter which the vials were charged with DMF (4.5 mL) and one of the following:
  4. stirringto stir under nitrogen for 35 min
  5. customThe reaction mixtures
  6. stirringto stir at ambient temperature
  7. customsamples were removed periodically
  8. customreaction kinetics

Sources & evidence

ORD record
ord-475aa84afd6c442bb689109156402f42
Source dataset
uspto-grants-2016_09
Patent number
US09440923B2

Linked notes

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