Sodium Hydroxide → 5-Bromo-6-methylpyridine-3-carboxylic acid

HRID 1619131Notes

Reaction equation

HRID 1619131 reaction equation
[OH-].[Na+].[Br:3][C:4]1[C:5]([CH3:15])=[N:6][CH:7]=[C:8]([CH:14]=1)[C:9]([O:11]CC)=[O:10]>C(O)C>[Br:3][C:4]1[C:5]([CH3:15])=[N:6][CH:7]=[C:8]([CH:14]=1)[C:9]([OH:11])=[O:10]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 58170478Ethyl 5-bromo-6-methyl-3-pyridinecarboxylate

Product 1

HCID 577808535-Bromo-6-methylpyridine-3-carboxylic acidYield 43.6%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

2M Aqueous sodium hydroxide solution (1.91 mL, 3.8 mmol) was added to a stirred solution of ethyl 5-bromo-6-methylnicotinate (preparation 47c, 0.41 g, 1.7 mmol) in ethanol (14 mL) at room temperature. After 3 hours, the solvent was evaporated and water was added to the residue. The pH was adjusted to 4-5 with concentrated hydrochloric acid and the mixture was extracted with ethyl acetate. The organic layer was washed with water, dried (MgSO4) and evaporated to give the title compound (0.16 g, 43%) as a white solid.

Workup

  1. customthe solvent was evaporated
  2. additionwater was added to the residue
  3. extractionthe mixture was extracted with ethyl acetate
  4. washThe organic layer was washed with water
  5. dry with materialdried (MgSO4)
  6. customevaporated

Sources & evidence

ORD record
ord-f9f8419b038a46c683c2f07808dde328
Source dataset
uspto-grants-2014_07
Patent number
US08772288B2

Reaction notes

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