Lithium hydroxide, monohydrate → 6-Bromo-3-methoxypyridine-2-carboxylic acid

HRID 2201525Notes

Reaction equation

HRID 2201525 reaction equation
[Br:1][C:2]1[N:7]=[C:6]([C:8]([O:10]C)=[O:9])[C:5]([O:12][CH3:13])=[CH:4][CH:3]=1.O[Li].O>O1CCOCC1.O>[Br:1][C:2]1[N:7]=[C:6]([C:8]([OH:10])=[O:9])[C:5]([O:12][CH3:13])=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 168937Lithium hydroxide, monohydrateHCID 70700803Methyl 6-bromo-3-methoxypyridine-2-carboxylate

Product 1

HCID 714639656-Bromo-3-methoxypyridine-2-carboxylic acidYield 74.2%

Reagents, catalysts & solvents 1

HCID 218864351,4-Dioxane--water (1/1)Solvent

Procedure

A solution of methyl 6-bromo-3-methoxypicolinate (3.0 g, 12.19 mmol) and LiOH.H2O (1.4 g, 33.36 mmol) in 1,4-dioxane/H2O (15 mL/15 mL) was stirred at RT overnight. The mixture was filtered and the filtrate was adjusted to pH=3 by aqueous HCl (2 M) and extracted with EtOAc. The combined organic phase was washed with brine, dried over Na2SO4 and concentrated to give the crude product of 6-bromo-3-methoxypicolinic acid (2.1 g, yield: 73%) without further purification. 1H-NMR (CDCl3, 400 MHz) δ 10.05 (br s, 1H), 7.70 (d, J=8.8 Hz, 1H), 7.40 (d, J=8.8 Hz, 1H), 4.01 (s, 3H). MS (M+H)+: 232/234.

Workup

  1. filtrationThe mixture was filtered
  2. extractionextracted with EtOAc
  3. washThe combined organic phase was washed with brine
  4. dry with materialdried over Na2SO4
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-953f57a4cf174d61b92d1ad6e008bd8d
Source dataset
uspto-grants-2016_06
Patent number
US09364482B2

Reaction notes

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