Sodium Hydroxide → 2-Pyridinecarboxylic acid, 4,5,6-trichloro-

HRID 1837439Notes

Reaction equation

HRID 1837439 reaction equation
[Cl:1][C:2]1[C:7]([Cl:8])=[C:6]([Cl:9])[N:5]=[C:4]([C:10]([O:12]C)=[O:11])[CH:3]=1.[OH-].[Na+]>O1CCOCC1.O>[Cl:1][C:2]1[C:7]([Cl:8])=[C:6]([Cl:9])[N:5]=[C:4]([C:10]([OH:12])=[O:11])[CH:3]=1

Participants

5

Reactant 2

HCID 14798Sodium Hydroxide2×HCID 12993691Methyl 4,5,6-trichloropicolinate

Product 1

HCID 129936922-Pyridinecarboxylic acid, 4,5,6-trichloro-Yield 94.3%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 312751,4-DioxaneSolvent

Conditions

Temperature
25 °C

Procedure

Methyl 4,5,6-trichloropyridine-2-carboxylate (10.11 g, 42 mmol) was suspended in dioxane (200 mL) and water (200 mL). To this mixture was added 1 N NaOH (42 mL, 42 mmol), and the reaction mixture was stirred at 25° C. After 72 h, 2 N NaOH (15 mL, 30 mmol) was added to drive the reaction to completion. The dioxane was removed by rotary evaporation, and the aqueous residue was acidified with concentrated hydrochloric acid. The precipitate was collected by suction filtration, washed with water and dried to provide 4,5,6-trichloropyridine-2-carboxylic acid (8.92 g, 39.6 mmol), mp 115-120° C.

Workup

  1. customthe reaction to completion
  2. customThe dioxane was removed by rotary evaporation
  3. filtrationThe precipitate was collected by suction filtration
  4. washwashed with water
  5. customdried

Sources & evidence

ORD record
ord-0b5bdedf5bfa4d779891f0340380c893
Source dataset
uspto-grants-2004_08
Patent number
US06784137B2

Reaction notes

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