Sodium Hydroxide → 3,4,6-Trichloro-2-pyridinecarboxylic acid

HRID 378785Notes

Reaction equation

HRID 378785 reaction equation
[Cl:1][C:2]1[C:3]([C:10]([O:12]C)=[O:11])=[N:4][C:5]([Cl:9])=[CH:6][C:7]=1[Cl:8].[OH-].[Na+]>CO>[Cl:1][C:2]1[C:3]([C:10]([OH:12])=[O:11])=[N:4][C:5]([Cl:9])=[CH:6][C:7]=1[Cl:8]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 22677534Methyl 3,4,6-trichloropyridine-2-carboxylate

Product 1

HCID 134540383,4,6-Trichloro-2-pyridinecarboxylic acidYield 93.1%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To methyl 3,4,6-Trichloropicolinate (3.57 g, 14.85 mmol) in 20 mL of methanol was added 1N NaOH (14.85 mL, 14.85 mmol). The reaction mixture was stirred at room temperature for 1 hr and then concentrated to dryness in vacuo. 100 mL each of diethyl ether and H2O were added. Aqueous layer was acidified with 1N HCl until pH=2. Methylene chloride was added and the aqueous phase was extracted with additional CH2Cl2 (2×100 mL). The combined extracts were dried (MgSO4) and concentrated to give 3.13 g of a white solid. 1H NMR(CDCl3): δ 7.50 (s, 1H).

Workup

  1. concentrationconcentrated to dryness in vacuo
  2. addition100 mL each of diethyl ether and H2O were added
  3. additionMethylene chloride was added
  4. extractionthe aqueous phase was extracted with additional CH2Cl2 (2×100 mL)
  5. dry with materialThe combined extracts were dried (MgSO4)
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-1b38e812deca4b08b94017f78a7e5129
Source dataset
uspto-grants-2001_10
Patent number
US06297197B1

Reaction notes

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