Hydrochloric Acid → (3-Methoxypyridin-2-yl)methanol

HRID 861615Notes

Reaction equation

HRID 861615 reaction equation
[OH-].[K+].Cl.[OH:4][C:5]1[C:6]([CH2:11][OH:12])=[N:7][CH:8]=[CH:9][CH:10]=1.[CH3:13]I.Cl>CS(C)=O>[OH:12][CH2:11][C:6]1[C:5]([O:4][CH3:13])=[CH:10][CH:9]=[CH:8][N:7]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 6328Methyl iodideHCID 14797Potassium HydroxideHCID 30841853-Hydroxy-2-(hydroxymethyl)pyridine hydrochloride

Product 1

HCID 5324774(3-Methoxypyridin-2-yl)methanolYield 32%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent2×

Procedure

Potassium hydroxide (41.66 g, 0.744 mol) was ground under nitrogen and stirred in DMSO (130 ml, anhydrous) for 20 min. 3-Hydroxy-2-hydroxymethyl pyridine hydrochloride [Aldrich] (47 g, 0.248 mol) was added and stirred for 30 min in an ice bath. Methyl iodide (35.2 g, 0.248 mol, 15.43 ml) in DMSO (20 ml) was added dropwise to the solution and then allowed to stir overnight at room temperature. 5N HCl was added to pH 1 and the solution was extracted with dichloromethane (5×500 ml). The aqueous was then basified with 5N NaOH to pH 14 and extracted with dichloromethane (3×500 ml). The organics (base wash) were dried over sodium sulfate, and concentrated leaving tan colored crystals. The solid was recrystallized (50% ethyl acetate/hexanes) providing 10.8 g (32%) of the titled product as light tan crystals:

Workup

  1. stirringto stir overnight at room temperature
  2. extractionthe solution was extracted with dichloromethane (5×500 ml)
  3. extractionextracted with dichloromethane (3×500 ml)
  4. washThe organics (base wash)
  5. dry with materialwere dried over sodium sulfate
  6. concentrationconcentrated
  7. customleaving tan colored crystals
  8. customThe solid was recrystallized (50% ethyl acetate/hexanes)

Sources & evidence

ORD record
ord-55dffc3bf41645d496be5e726cbe8e62
Source dataset
uspto-grants-1998_02
Patent number
US05714503

Reaction notes

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