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

HRID 595552Notes

Reaction equation

HRID 595552 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 81%

Reagents, catalysts & solvents 1

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

Procedure

A mixture of methyl 6-bromo-3-methoxypicolinate (4 g, 18.4 mmol) and LiOH—H2O (1.6 g, 36.9 mmol) in dioxane/H2O (5/1, 40 mL) was stirred at RT overnight. After pH was adjusted to 7, the mixture was filtered to provide crude 6-bromo-3-methoxypicolinic acid (3.1 g, yield: 81%). 1H-NMR (CDCl3, 400 MHz) δ 10.71 (m, 1H), 7.70 (d, J=8.0 Hz, 1H), 7.40 (d, J=8.0 Hz, 1H), 4.01 (s, 3H). MS (M+H)+: 232/234.

Workup

  1. filtrationthe mixture was filtered

Sources & evidence

ORD record
ord-0d01bed6d81645a6a0315a1da2d1be1e
Source dataset
uspto-grants-2016_01
Patent number
US09242998B2

Reaction notes

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