Methanol → HCID 57516329, compound

HRID 1810982Notes

Reaction equation

HRID 1810982 reaction equation
C[O:2][C:3](=[O:12])[C:4]1[CH:9]=[C:8]([F:10])[C:7]([CH3:11])=[N:6][CH:5]=1.CO.[OH-].[Na+]>O>[F:10][C:8]1[C:7]([CH3:11])=[N:6][CH:5]=[C:4]([CH:9]=1)[C:3]([OH:12])=[O:2]

Participants

5

Reactant 3

HCID 887MethanolHCID 14798Sodium HydroxideHCID 575163283-Pyridinecarboxylic acid, 5-fluoro-6-methyl-, methyl ester

Product 1

HCID 57516329HCID 57516329, compoundYield 88.4%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
50 °C

Procedure

To a suspension of 5-fluoro-6-methyl-nicotinic acid methyl ester (0.21 g, 1.24 mmol) in a 1:1 mixture of MeOH:water (20 mL) is added sodium hydroxide as a 10% aqueous solution (1.0 mL, 2.5 mmol). The mixture is heated to 50° C. for 1 h then cooled to room temperature and concentrated under reduced pressure to remove volatile organics. The pH of the resulting solution is adjusted to slightly acidic (approximately pH 5) by the addition of a 2N solution of HCl. The mixture is extracted with EtOAc and the combined organic phase is dried over anhydrous sodium sulfate and concentrated to provide 0.170 g of 5-fluoro-6-methyl-nicotinic acid as a solid.

Workup

  1. temperaturethen cooled to room temperature
  2. concentrationconcentrated under reduced pressure
  3. customto remove volatile organics
  4. additionby the addition of a 2N solution of HCl
  5. extractionThe mixture is extracted with EtOAc
  6. dry with materialthe combined organic phase is dried over anhydrous sodium sulfate
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-ad44ce75f6274c3c855db5834e44fef5
Source dataset
uspto-grants-2013_01
Patent number
US08362249B2

Reaction notes

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