Sodium Hydroxide → 5-(2,2,2-Trifluoroethoxy)pyridine-2-carboxylic acid
Reaction equation
[F:1][C:2]([F:16])([F:15])[CH2:3][O:4][C:5]1[CH:6]=[CH:7][C:8]([C:11]([O:13]C)=[O:12])=[N:9][CH:10]=1.[OH-].[Na+]>CO>[F:16][C:2]([F:1])([F:15])[CH2:3][O:4][C:5]1[CH:6]=[CH:7][C:8]([C:11]([OH:13])=[O:12])=[N:9][CH:10]=1Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Procedure
Methyl 5-(2,2,2-trifluoroethoxy)pyridine-2-carboxylate (Intermediate 223, 0.650 g, 2.77 mmol) was dissolved in MeOH (10 mL), 2M aq. sodium hydroxide (3.46 mL, 6.93 mmol) was added and the mixture stirred at room temperature for 2 h. MeOH was removed under vacuum and the aqueous suspension neutralised by adding 2M aq. hydrochloric acid (3.5 mL). The resultant precipitate was filtered, washed with diethyl ether and dried under vacuum to afford the title compound as a white solid (0.179 mg, 29%). 1H NMR (500 MHZ, MeOH-d4) δ ppm 8.41 (1H, d), 8.15 (1H, d), 7.59 (1H, dd) and 4.77 (2H, q).