Methanol → 6-Methoxynicotinic acid

HRID 235850Notes

Reaction equation

HRID 235850 reaction equation
Cl[C:2]1[N:7]=[CH:6][C:5]([C:8]([OH:10])=[O:9])=[CH:4][CH:3]=1.[CH3:11][OH:12]>C[O-].[Na+]>[CH3:11][O:12][C:2]1[N:7]=[CH:6][C:5]([C:8]([OH:10])=[O:9])=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 887MethanolHCID 792226-Chloronicotinic acid

Product 1

HCID 5924996-Methoxynicotinic acid

Reagents, catalysts & solvents 1

HCID 10942334Sodium MethoxideSolvent

Procedure

To a suspension of 6-chloropyridine-3-carboxylic acid (4.15 g) in methanol (40 cc), 4 M methanolic sodium methylate solution (40 cc) is added. The mixture is heated under reflux for 60 hours. The solvent is distilled off under reduced pressure (4 kPa). The residue is taken up in distilled water (100 cc) and the mixture is acidified to pH 5 with hydrochloric acid in 11.9 M aqueous solution. The precipitate produced is separated by filtration, washed with distilled water (5×10 cc) and dried in the air. 6-Methoxypyridine-3-carboxylic acid (3.3 g) is produced, m.p. 180° C.

Workup

  1. additionis added
  2. temperatureThe mixture is heated
  3. temperatureunder reflux for 60 hours
  4. distillationThe solvent is distilled off under reduced pressure (4 kPa)
  5. customThe precipitate produced
  6. customis separated by filtration
  7. washwashed with distilled water (5×10 cc)
  8. customdried in the air

Sources & evidence

ORD record
ord-25f2f5f4775e4709968269a240fc8baa
Source dataset
uspto-grants-1987_02
Patent number
US04642308

Reaction notes

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