Methanol → 6-Chloro-3-methylpyridine-2-carboxylic acid

HRID 239911Notes

Reaction equation

HRID 239911 reaction equation
[OH-].[Na+].[Cl:3][C:4]1[N:9]=[C:8]([C:10]([O:12]C)=[O:11])[C:7]([CH3:14])=[CH:6][CH:5]=1.CO>C1COCC1>[Cl:3][C:4]1[N:9]=[C:8]([C:10]([OH:12])=[O:11])[C:7]([CH3:14])=[CH:6][CH:5]=1

Participants

5

Reactant 3

HCID 887MethanolHCID 14798Sodium HydroxideHCID 45489870Methyl 6-chloro-3-methylpyridine-2-carboxylate

Product 1

HCID 469414706-Chloro-3-methylpyridine-2-carboxylic acidYield 84.3%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of aqueous 1N NaOH (10 ml) is added to a stirred solution of methyl 6-chloro-3-methyl-pyridine-2-carboxylate (1.0 g, 5.39 mmoles) in THF:MeOH (10 ml:2 ml). The mixture is stirred at room temperature for 3 hours. The organic solvent is removed under reduced pressure and the semi-solid is dissolved in water and acidified to pH 1-2 with aqueous 1N HCl. The resulting precipitate is filtered, washed with water, and dried at 40° C. in a vacuum oven for 12 hours to give the title compound as a white solid (780 mg, 84%). Mass spectrum (m/z): 172.0 (M+1).

Workup

  1. customThe organic solvent is removed under reduced pressure
  2. dissolutionthe semi-solid is dissolved in water
  3. filtrationThe resulting precipitate is filtered
  4. washwashed with water
  5. customdried at 40° C. in a vacuum oven for 12 hours

Sources & evidence

ORD record
ord-574b1116db0c44c19422f73110138fb5
Source dataset
uspto-grants-2014_02
Patent number
US08642768B2

Reaction notes

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