Sodium Hydroxide → Sodium 5-methoxypicolinate

HRID 1526576Notes

Reaction equation

HRID 1526576 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[CH:5][C:6]([C:9]([O:11]C)=[O:10])=[N:7][CH:8]=1.[OH-].[Na+:14]>>[CH3:1][O:2][C:3]1[CH:4]=[CH:5][C:6]([C:9]([O-:11])=[O:10])=[N:7][CH:8]=1.[Na+:14]

Participants

3

Reactant 2

HCID 14798Sodium HydroxideHCID 14282457Methyl 5-methoxypyridine-2-carboxylate

Product 1

HCID 90389396Sodium 5-methoxypicolinateYield 97%

Conditions

Temperature
120 °C

Procedure

A microwave vial was charged with methyl 5-methoxypicolinate (9.700 g, 58.0 mmol, synthesized according to Tetrahedron Letters 2011, 52, 122-124) and sodium hydroxide solution (10 N; 58.0 ml, 580 mmol). The reaction mixture was stirred and heated in a CEM Voyager microwave (Large-Scale Unit) at 120° C. for 11 min (150 watts, Powermax feature on). Subsequently, the reaction mixture was allowed to stir for 10 minutes at ambient temperature. The precipitate was collected by filtration and the solid was rinsed with hexanes. The solid was dried to obtain sodium 5-methoxypicolinate (9.83 g, 56.1 mmol, 97% yield) as a light-yellow solid. MS m/z=175.9 [M+H]+. Calculated for C7H6NNaO3: 175. 1H NMR (400 MHz, MeOH) d ppm 8.23 (d, J=2.93 Hz, 1H) 8.06 (d, J=8.61 Hz, 1H) 7.39 (dd, J=8.80, 2.93 Hz, 1H) 3.91 (s, 3H)

Workup

  1. stirringto stir for 10 minutes at ambient temperature
  2. filtrationThe precipitate was collected by filtration
  3. washthe solid was rinsed with hexanes
  4. customThe solid was dried

Sources & evidence

ORD record
ord-a365b005aa384efdbcd578380c93f795
Source dataset
uspto-grants-2015_07
Patent number
US09085576B2

Reaction notes

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