Sodium Hydroxide → 2-[N-(2-(2-thienylmethoxy)-5-bromobenzyl)-N-ethylamino]pyridine-5-carboxylic acid
Reaction equation
[S:1]1[CH:5]=[CH:4][CH:3]=[C:2]1[CH2:6][O:7][C:8]1[CH:27]=[CH:26][C:25]([Br:28])=[CH:24][C:9]=1[CH2:10][N:11]([C:14]1[CH:19]=[CH:18][C:17]([C:20]([O:22]C)=[O:21])=[CH:16][N:15]=1)[CH2:12][CH3:13].[OH-].[Na+]>CO>[S:1]1[CH:5]=[CH:4][CH:3]=[C:2]1[CH2:6][O:7][C:8]1[CH:27]=[CH:26][C:25]([Br:28])=[CH:24][C:9]=1[CH2:10][N:11]([C:14]1[CH:19]=[CH:18][C:17]([C:20]([OH:22])=[O:21])=[CH:16][N:15]=1)[CH2:12][CH3:13]Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Procedure
A solution of methyl 2-[N-(2-(2-thienylmethoxy)-5-bromobenzyl)-N-ethylamino]pyridine-5-carboxylate (0.53 g, 1.15 mmol) in methanol (25 mL) was treated with aqueous sodium hydroxide (2N, 5 mL). The reaction was heated to reflux for 9 hours. The reaction mixture was cooled and evaporated and residue was diluted with water and acidified with acetic acid. The off-white solid was filtered off to give 2-[N-(2-(2-thienylmethoxy)-5-bromobenzyl)-N-ethylamino]pyridine-5-carboxylic acid (0.41 g, 91%).