Lithium hydroxide, monohydrate → 5-Fluoro-3-methylpicolinic acid

HRID 1186207Notes

Reaction equation

HRID 1186207 reaction equation
C[O:2][C:3]([C:5]1[C:10]([CH3:11])=[CH:9][C:8]([F:12])=[CH:7][N:6]=1)=[O:4].O.[OH-].[Li+]>CO.O>[F:12][C:8]1[CH:9]=[C:10]([CH3:11])[C:5]([C:3]([OH:4])=[O:2])=[N:6][CH:7]=1

Participants

5

Reactant 2

HCID 168937Lithium hydroxide, monohydrateHCID 58563046Methyl 5-fluoro-3-methylpyridine-2-carboxylate

Product 1

HCID 582246285-Fluoro-3-methylpicolinic acidYield 86.9%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent2×

Procedure

To a solution of 5-fluoro-3-methyl-pyridine-2-carboxylic acid methyl ester (1.28 g) in MeOH (6 ml) was added at 22° C. a solution of lithium hydroxide mono hydrate (636 mg) in water (3 ml) and stiring was continued for 16 h. The mixture was diluted with water, the MeOH was evaporated at reduced pressure and the pH was adjusted to 1 using 1 N aqueous HCl. The aqueous layer was extracted with AcOEt, the organic layer was dried, evaporated and the residue was crystallized from AcOEt/n-heptane to give the title compound (1.02 g) as a pale yellow solid. MS: m/z=153.7 [M−H]−.

Workup

  1. customthe MeOH was evaporated at reduced pressure
  2. extractionThe aqueous layer was extracted with AcOEt
  3. customthe organic layer was dried
  4. customevaporated
  5. customthe residue was crystallized from AcOEt/n-heptane

Sources & evidence

ORD record
ord-0fb1492b483b44eb80ec393f1987a487
Source dataset
uspto-grants-2014_03
Patent number
US08673894B2

Reaction notes

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