Sodium Hydroxide → (2-(2-Chloro-6-methylphenylamino)-7-fluoro-6-benzoxazolyl)acetic acid

HRID 1372641Notes

Reaction equation

HRID 1372641 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]=1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 58778824Methyl (2-(2-chloro-6-methylphenylamino)-7-fluoro-6-benzoxazolyl)acetate

Product 1

HCID 17859500(2-(2-Chloro-6-methylphenylamino)-7-fluoro-6-benzoxazolyl)acetic acidYield 93.4%

Reagents, catalysts & solvents 1

HCID 21899815MeOH tetrahydrofuranSolvent

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.

Workup

  1. distillationthe reaction 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-ade70f6e237d4bb9aadf133fb61bcfc8
Source dataset
uspto-grants-2007_01
Patent number
US07157487B2

Reaction notes

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