Lithium Hydroxide → 2-(3-(3-Hexylquinoline-8-carboxamido)phenoxy)acetic acid
Reaction equation
[OH-].[Li+].[CH2:3]([C:9]1[CH:10]=[N:11][C:12]2[C:17]([CH:18]=1)=[CH:16][CH:15]=[CH:14][C:13]=2[C:19]([NH:21][C:22]1[CH:23]=[C:24]([CH:33]=[CH:34][CH:35]=1)[O:25][CH2:26][C:27]([O:29]C(C)C)=[O:28])=[O:20])[CH2:4][CH2:5][CH2:6][CH2:7][CH3:8]>O>[CH2:3]([C:9]1[CH:10]=[N:11][C:12]2[C:17]([CH:18]=1)=[CH:16][CH:15]=[CH:14][C:13]=2[C:19]([NH:21][C:22]1[CH:23]=[C:24]([CH:33]=[CH:34][CH:35]=1)[O:25][CH2:26][C:27]([OH:29])=[O:28])=[O:20])[CH2:4][CH2:5][CH2:6][CH2:7][CH3:8]Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Procedure
Aqueous 2 N lithium hydroxide (0.7 mL, 1.4 mmol) and water (0.7 mL) were added to a solution of isopropyl 2-(3-(3-hexylquinoline-8-carboxamido)phenoxy)acetate (210 mg, 0.47 mmol) in THE (5.0 mL) and the solution was stirred at room temperature. After 20 h, the THF was removed in vacuo. The residual aqueous phase was adjusted to pH 4-5 with 1 N aqueous HCl and extracted with EtOAc (3×). The combined organic phase was dried (MgSO4), filtered and concentrated in vacuo to afford 177 mg (93%) of the title compound.