Water → 2-Methoxy-4-methylpyridine

HRID 1410033Notes

Reaction equation

HRID 1410033 reaction equation
Cl[C:2]1[CH:7]=[C:6]([CH3:8])[CH:5]=[CH:4][N:3]=1.[O:9]([CH3:11])[Na].O>CS(C)=O>[CH3:11][O:9][C:2]1[CH:7]=[C:6]([CH3:8])[CH:5]=[CH:4][N:3]=1

Participants

5

Reactant 3

HCID 962WaterHCID 772482-Chloro-4-methylpyridineHCID 178418582HCID 178418582, compound

Product 1

HCID 142234722-Methoxy-4-methylpyridineYield 46.8%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Conditions

Temperature
100 °C

Procedure

A mixture of 2-chloro-4-methylpyridine (20 g, 0.156 mol) and NaOCH3 (9.3 g, 0.172 mol) in DMSO (200 mL) was stirred at 100° C. for 4 hours. The solution was added to H2O and then extracted with ethyl acetate (50 mL×2). The organic layer was washed with H2O (300 mL) brine (300 mL) and dried concentrated to give 2-methoxy-4-methylpyridine (9 g, 46%). LC-MS: 124 [M+H]+, tR=1.21 min.

Workup

  1. extractionextracted with ethyl acetate (50 mL×2)
  2. washThe organic layer was washed with H2O (300 mL) brine (300 mL)
  3. customdried
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-a0838bff0a754ad09f228882450d6756
Source dataset
uspto-grants-2014_12
Patent number
US08921383B2

Reaction notes

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