Sodium Hydroxide → (2-(2-Chloro-6-methylphenylamino)-7-fluoro-6-benzoxazolyl)acetic acid
Reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([CH3:8])[C:3]=1[NH:9][C:10]1[O:11][C:12]2[C:18]([F:19])=[C:17]([CH2:20][C:21]([O:23]C)=[O:22])[CH:16]=[CH:15][C:13]=2[N:14]=1.[OH-].[Na+]>C1COCC1.CO>[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([CH3:8])[C:3]=1[NH:9][C:10]1[O:11][C:12]2[C:18]([F:19])=[C:17]([CH2:20][C:21]([OH:23])=[O:22])[CH:16]=[CH:15][C:13]=2[N:14]=1Participants
4
Procedure
To a solution of methyl (2-(2-chloro-6-methylphenylamino)-7-fluoro-6-benzoxazolyl)acetate (1.45 g, 4.16 mmol) in THF/methanol (4:1, v/v 100 ml) was added 1N NaOH (40 ml). After stirring at room temperature for 17 hours, the reaction mixture was distilled under reduced pressure to remove the solvent. The residue was acidified with 1N HCl. The crystals thus precipitated were collected by filtration under reduced pressure, washed with water and dried under reduced pressure to give (2-(2-chloro-6-methylphenylamino)-7-fluoro-6-benzoxazolyl)acetic acid (1.30 g, 93%) as a colorless crystalline powder.