Methanol → 2-(Hydroxymethyl)pyridine-4-carbonitrile

HRID 1049472Notes

Reaction equation

HRID 1049472 reaction equation
[C:1]([C:3]1[CH:8]=[CH:7][N:6]=[CH:5][CH:4]=1)#[N:2].S(=O)(=O)(O)O.[NH4+].[NH4+].[O-]S(OOS([O-])(=O)=O)(=O)=O.[CH3:26][OH:27]>O>[OH:27][CH2:26][C:5]1[CH:4]=[C:3]([CH:8]=[CH:7][N:6]=1)[C:1]#[N:2]

Participants

6

Reactant 4

HCID 887MethanolHCID 1118Sulfuric AcidHCID 75064-CyanopyridineHCID 62648Ammonium Persulfate

Product 1

HCID 132925992-(Hydroxymethyl)pyridine-4-carbonitrile

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a solution of 4-cyanopyridine (10.4 g) in methanol (180 mL), a solution of conc. sulfuric acid (6.98 mL) in water (90 mL) and ammonium peroxodisulfate (45.6 g) were successively added at room temperature, and the mixture was heated under reflux for 14 hr. The solvent was evaporated under reduced pressure, and 28% aqueous ammonia (40 mL) was added. The reaction mixture was extracted with a mixed solvent of ethyl acetate and THF, and the extract was washed with saturated brine, and dried over anhydrous magnesium sulfate. The solvent was evaporated under reduced pressure and the residue was purified by silica gel column chromatography (ethyl acetate/hexane) to give the title compound (5.08 g) as a pale-yellow solid.

Workup

  1. temperaturethe mixture was heated
  2. temperatureunder reflux for 14 hr
  3. customThe solvent was evaporated under reduced pressure, and 28% aqueous ammonia (40 mL)
  4. additionwas added
  5. extractionThe reaction mixture was extracted with a mixed solvent of ethyl acetate and THF
  6. washthe extract was washed with saturated brine
  7. dry with materialdried over anhydrous magnesium sulfate
  8. customThe solvent was evaporated under reduced pressure
  9. customthe residue was purified by silica gel column chromatography (ethyl acetate/hexane)

Sources & evidence

ORD record
ord-66e30d0d049141dda353ccc5dabbad18
Source dataset
uspto-grants-2016_07
Patent number
US09382188B2

Reaction notes

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