Sodium Hydroxide → (2-(5-Fluoro-2-methylphenylamino)-6-benzoxazolyl)acetic acid

HRID 1372639Notes

Reaction equation

HRID 1372639 reaction equation
[F:1][C:2]1[CH:3]=[CH:4][C:5]([CH3:23])=[C:6]([NH:8][C:9]2[O:10][C:11]3[CH:17]=[C:16]([CH2:18][C:19]([O:21]C)=[O:20])[CH:15]=[CH:14][C:12]=3[N:13]=2)[CH:7]=1.[OH-].[Na+]>C1COCC1.CO>[F:1][C:2]1[CH:3]=[CH:4][C:5]([CH3:23])=[C:6]([NH:8][C:9]2[O:10][C:11]3[CH:17]=[C:16]([CH2:18][C:19]([OH:21])=[O:20])[CH:15]=[CH:14][C:12]=3[N:13]=2)[CH:7]=1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 58778736Methyl (2-(5-fluoro-2-methylphenylamino)-6-benzoxazolyl)acetate

Product 1

HCID 17858906(2-(5-Fluoro-2-methylphenylamino)-6-benzoxazolyl)acetic acidYield 97%

Reagents, catalysts & solvents 1

HCID 21899815MeOH tetrahydrofuranSolvent

Procedure

To a solution of methyl (2-(5-fluoro-2-methylphenylamino)-6-benzoxazolyl)acetate (1.73 g, 5.50 mmol) in THF/methanol (2:1, 30 ml) was added 1N NaOH (20 ml). After stirring at room temperature for 3.5 hours, the 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-(5-fluoro-2-methylphenylamino)-6-benzoxazolyl)acetic acid (1.60 g, 97%) as a colorless crystalline powder.

Workup

  1. distillationthe mixture was distilled under reduced pressure
  2. customto remove the solvent
  3. customThe crystals thus precipitated
  4. filtrationwere collected by filtration under reduced pressure
  5. washwashed with water
  6. customdried under reduced pressure

Sources & evidence

ORD record
ord-9e8267cfa4654f088a21dfdd2e6cff48
Source dataset
uspto-grants-2007_01
Patent number
US07157487B2

Reaction notes

Loading…