2-Methoxyethanol → 2-(2-methoxyethoxy)pyridine-3-carboxylic acid

HRID 2271053Notes

Reaction equation

HRID 2271053 reaction equation
CC(C)([O-])C.[K+].Cl[C:8]1[N:16]=[CH:15][CH:14]=[CH:13][C:9]=1[C:10]([OH:12])=[O:11].[CH3:17][O:18][CH2:19][CH2:20][OH:21]>>[CH3:17][O:18][CH2:19][CH2:20][O:21][C:8]1[C:9]([C:10]([OH:12])=[O:11])=[CH:13][CH:14]=[CH:15][N:16]=1

Participants

4

Reactant 3

HCID 80192-MethoxyethanolHCID 762582-Chloronicotinic acidHCID 23665647Potassium tert-butoxide

Product 1

HCID 187561882-(2-methoxyethoxy)pyridine-3-carboxylic acidYield 81%

Procedure

Potassium t-butoxide (45.0 g, 0.40 mol) was added portion-wise to ice-cold 2-methoxyethanol (175 ml), and the resulting solution added to a suspension of 2-chloronicotinic acid (30.0 g, 0.19 mol) in 2-methoxyethanol (175 ml). The reaction mixture was heated under reflux for 26 hours, then cooled and concentrated under reduced pressure. The residue was diluted with water (200 ml), the pH of the solution adjusted to 5 using concentrated hydrochloric acid, and extracted with dichloromethane (3×). The combined organic extracts were washed with brine, dried (MgSO4), evaporated under reduced pressure and azeotroped with toluene, to afford the title compound, (30.54 g, 81%).

Workup

  1. temperatureThe reaction mixture was heated
  2. temperatureunder reflux for 26 hours
  3. temperaturecooled
  4. concentrationconcentrated under reduced pressure
  5. additionThe residue was diluted with water (200 ml)
  6. extractionextracted with dichloromethane (3×)
  7. washThe combined organic extracts were washed with brine
  8. dry with materialdried (MgSO4)
  9. customevaporated under reduced pressure
  10. customazeotroped with toluene

Sources & evidence

ORD record
ord-1f50cb220fbe490fbff77347e66469a8
Source dataset
uspto-grants-2001_12
Patent number
US06333330B1

Reaction notes

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