Methanol → Methyl 4-methoxypyridine-2-carboxylate

HRID 985526Notes

Reaction equation

HRID 985526 reaction equation
Cl.[CH3:2][O:3][C:4]([C:6]1[CH:11]=[C:10](Cl)[CH:9]=[CH:8][N:7]=1)=[O:5].[CH3:13][OH:14]>>[CH3:2][O:3][C:4]([C:6]1[CH:11]=[C:10]([O:14][CH3:13])[CH:9]=[CH:8][N:7]=1)=[O:5]

Participants

3

Reactant 2

HCID 887MethanolHCID 16655470Methyl 4-chloropyridine-2-carboxylate--hydrogen chloride (1/1)

Product 1

HCID 1519345Methyl 4-methoxypyridine-2-carboxylateYield 88%

Procedure

4-Chloropyridine-2-carboxylic acid methyl ester hydrochloride (25 g, 0.12 mol) was dissolved in methanol (200 ml) and heated at reflux for 66 h. The solvent was evaporated and the residue partitioned between dichloromethane and saturated sodium hydrogencarbonate solution. The organic layer was washed with brine, dried over sodium sulphate and concentrated to give 4-methoxypyridine-2-carboxylic acid methyl ester (17.6 g, 88%) as a yellow crystalline solid. 1H NMR (360 MHz, CDCl3) δH 3.91 (3H, s), 4.02 (3H, s), 6.98 (1H, dd, J 3 and 6), 7.67 (1H, d, J 3), 8.54 (1H, d, J 6).

Workup

  1. temperatureheated
  2. temperatureat reflux for 66 h
  3. customThe solvent was evaporated
  4. customthe residue partitioned between dichloromethane and saturated sodium hydrogencarbonate solution
  5. washThe organic layer was washed with brine
  6. dry with materialdried over sodium sulphate
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-0319c8dcfd8a44298fc8b58cd6c27301
Source dataset
uspto-grants-2005_03
Patent number
US06872731B2

Reaction notes

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