Methanol → Methyl 4-methoxypyridine-2-carboxylate

HRID 399478

Reaction equation

HRID 399478 reaction equation
Cl[C:2]1[CH:7]=[CH:6][N:5]=[C:4]([C:8]([O:10][CH3:11])=[O:9])[CH:3]=1.[Na].[CH3:13][OH:14]>>[CH3:13][O:14][C:2]1[CH:7]=[CH:6][N:5]=[C:4]([C:8]([O:10][CH3:11])=[O:9])[CH:3]=1

Participants

4

Reactant 3

HCID 887MethanolHCID 820890Methyl 4-ChloropicolinateHCID 5360545Sodium

Product 1

HCID 1519345Methyl 4-methoxypyridine-2-carboxylate

Procedure

A mixture of methyl 4-chloropyridine-2-carboxylate (3.7 g), sodium metal (0.5 g) and methanol (100 ml) was stirred and heated to reflux for 8 hours. The mixture was evaporated and the residue was partitioned between ethyl acetate and water. The organic phase was dried (MgSO4) and evaporated to give methyl 4-methoxypyridine-2-carboxylate (3 g).

Workup

  1. temperatureheated
  2. temperatureto reflux for 8 hours
  3. customThe mixture was evaporated
  4. customthe residue was partitioned between ethyl acetate and water
  5. dry with materialThe organic phase was dried (MgSO4)
  6. customevaporated

Sources & evidence

ORD record
ord-20b68bca3eea4b289fb28d8fe1e448c8
Source dataset
uspto-grants-1998_10
Patent number
US05821246

Linked notes

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