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

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

Reactant 3

HCID 80192-Methoxyethanol

HCID 762582-Chloronicotinic acid

HCID 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%).