3-Acetoxy-6-fluoro-5-methylpyridine → 6-Fluoro-5-methylpyridin-3-ol

HRID 367071

Reaction equation

HRID 367071 reaction equation
C([O:4][C:5]1[CH:6]=[N:7][C:8]([F:12])=[C:9]([CH3:11])[CH:10]=1)(=O)C>[OH-].[Na+]>[F:12][C:8]1[C:9]([CH3:11])=[CH:10][C:5]([OH:4])=[CH:6][N:7]=1

Participants

3

Reactant 1

HCID 224516053-Acetoxy-6-fluoro-5-methylpyridine

Product 1

HCID 229897166-Fluoro-5-methylpyridin-3-olYield 87%

Reagents, catalysts & solvents 1

HCID 14798Sodium HydroxideSolvent

Procedure

The product of step 32d (3.6 g, 21.3 mmol) was dissolved in 20% aqueous NaOH (25 mL). After complete consumption of the starting material the solution was neutralized by addition of HCl. The aqueous mixture was extracted with ethyl acetate. The organic extracts were dried (MgSO4), and the solvent was evaporated. The crude product was triturated with hexane to yield 2.35 g (87%) of the title compound: MS (CI/NH3) m/z: 128 (M+H)+, 145 (M+NH4)+ ; 1H NMR (CDCl3, 300 MHz) δ: 7.61(t, J=2.2 Hz, 1H), 7.17 (m, 1 H), 2.25 (s, 3H).

Workup

  1. customAfter complete consumption of the starting material the solution
  2. additionwas neutralized by addition of HCl
  3. extractionThe aqueous mixture was extracted with ethyl acetate
  4. dry with materialThe organic extracts were dried (MgSO4)
  5. customthe solvent was evaporated
  6. customThe crude product was triturated with hexane

Sources & evidence

ORD record
ord-c229255d6d3c4668a0b36798cf316587
Source dataset
uspto-grants-2000_10
Patent number
US06133253

Linked notes

Loading…