Sodium Hydroxide → 5,6-Dichloronicotinic acid

HRID 1849494Notes

Reaction equation

HRID 1849494 reaction equation
[Cl:1][C:2]1[C:3]([Cl:13])=[N:4][CH:5]=[C:6]([CH:12]=1)[C:7]([O:9]CC)=[O:8].[OH-].[Na+]>C1COCC1.CO.O>[Cl:1][C:2]1[C:3]([Cl:13])=[N:4][CH:5]=[C:6]([CH:12]=1)[C:7]([OH:9])=[O:8]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 16762519Ethyl 5,6-Dichloronicotinate

Product 1

HCID 2479875,6-Dichloronicotinic acidYield 92.6%

Reagents, catalysts & solvents 1

HCID 21892291Methanol tetrahydrofuran waterSolvent

Procedure

A mixture of ethyl 5,6-dichloronicotinate (1.0 g, 4.5 mmol) and aqueous NaOH (2 N, 6.75 mL, 13.5 mmol) in a mixed solvents of THF/MeOH/water (50 mL, 4/1/1) was stirred at room temperature for 0.5 h. After concentration, the mixture was acidified with 2 N HCl to pH around 2. The resulting mixture was extracted with ether (30 mL×3). The organic layer was washed with water (50 mL×3), dried over Na2SO4, and concentrated to afford 5,6-dichloronicotinic acid (800 mg, 91% yield) as a white solid. LCMS (ESI) m/z: 192.0 [M+H]+.

Workup

  1. concentrationAfter concentration
  2. extractionThe resulting mixture was extracted with ether (30 mL×3)
  3. washThe organic layer was washed with water (50 mL×3)
  4. dry with materialdried over Na2SO4
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-76aedf6f75294971862b9a30ad735e39
Source dataset
uspto-grants-2015_02
Patent number
US08952169B2

Reaction notes

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