Sodium Hydroxide → 5-(2-Hydroxypropan-2-yl)nicotinic acid
Reaction equation
[OH:1][C:2]([C:5]1[CH:6]=[C:7]([C:11]([O:13]C)=[O:12])[CH:8]=[N:9][CH:10]=1)([CH3:4])[CH3:3].[OH-].[Na+]>CO>[OH:1][C:2]([C:5]1[CH:6]=[C:7]([C:11]([OH:13])=[O:12])[CH:8]=[N:9][CH:10]=1)([CH3:3])[CH3:4]Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Procedure
To a solution of methyl 5-(2-hydroxypropan-2-yl)pyridine-3-carboxylate (0.179 g, 0.915 mmol) in methanol (4.57 mL) was added 1 N aqueous sodium hydroxide solution (2.74 mL, 2.74 mmol). The reaction was stirred at room temperature for 30 min and then concentrated under reduced pressure. The resulting residue was acidified via the addition of 1 N aqueous hydrogen chloride solution until the pH was 2. Ethyl acetate was then added, and the extracted organics were dried over magnesium sulfate, filtered and concentrated to provide the title compound: LCMS m/z 182.01 [M+H]+; 1H NMR (500 MHz, CD3OD) δ 8.91 (s, 1 H), 8.79 (d, J=1.8 Hz, 1 H), 8.43 (d, J=1.9 Hz, 1 H), 1.51 (s, 6 H).