Lithium Hydroxide → 6-Bromo-3-hydroxypyridine-2-carboxylic acid

HRID 2178278Notes

Reaction equation

HRID 2178278 reaction equation
[Br:1][C:2]1[N:7]=[C:6]([C:8]([O:10]C)=[O:9])[C:5]([OH:12])=[CH:4][CH:3]=1.[Li+].[OH-]>CO>[Br:1][C:2]1[N:7]=[C:6]([C:8]([OH:10])=[O:9])[C:5]([OH:12])=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 3939Lithium HydroxideHCID 22175135Methyl 6-bromo-3-hydroxypicolinate

Product 1

HCID 221751166-Bromo-3-hydroxypyridine-2-carboxylic acid

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Methyl 6-bromo-3-hydroxypicolinate (26B) (464 mg, 2 mmol) in MeOH (0.5 mL) was added to a solution of LiOH (200 mg in 2 mL water). The reaction mixture was stirred at rt for 2 h. The product precipitated out of solution and was filtered, washed with water, and dried under reduced pressure to provide the desired product 6-bromo-3-hydroxypicolinic acid (55A). 1H NMR (300 MHz, CDCl3): 7.6 (1H, d), 7.32 (1H, d).

Workup

  1. customThe product precipitated out of solution
  2. filtrationwas filtered
  3. washwashed with water
  4. customdried under reduced pressure

Sources & evidence

ORD record
ord-02d113a9a0864c5aa00ff2521cf38f57
Source dataset
uspto-grants-2015_06
Patent number
US09067928B2

Reaction notes

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