Sodium Hydroxide → (2-(1-Naphthylamino)-7-fluoro-6-benzoxazolyl)acetic acid

HRID 1372658Notes

Reaction equation

HRID 1372658 reaction equation
[C:1]1([NH:11][C:12]2[O:13][C:14]3[C:20]([F:21])=[C:19]([CH2:22][C:23]([O:25]C)=[O:24])[CH:18]=[CH:17][C:15]=3[N:16]=2)[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][CH:2]=1.[OH-].[Na+]>C1COCC1.CO>[C:1]1([NH:11][C:12]2[O:13][C:14]3[C:20]([F:21])=[C:19]([CH2:22][C:23]([OH:25])=[O:24])[CH:18]=[CH:17][C:15]=3[N:16]=2)[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][CH:2]=1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 58779085Methyl (2-(1-naphthylamino)-7-fluoro-6-benzoxazolyl)acetate

Product 1

HCID 17859496(2-(1-Naphthylamino)-7-fluoro-6-benzoxazolyl)acetic acidYield 106.5%

Reagents, catalysts & solvents 1

HCID 21899815MeOH tetrahydrofuranSolvent

Procedure

Methyl (2-(1-naphthylamino)-7-fluoro-6-benzoxazolyl)acetate (1.41 g, 4.02 mmol) was dissolved in THF/methanol (21, 30 ml). To the resulting solution was added 1N NaOH (10 ml). After stirring at room temperature for 12 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-(1-naphthylamino)-7-fluoro-6-benzoxazolyl)acetic acid (1.44 g, 100%) as a brown solid.

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-af96dadc91f64ff1976115f4d08df4c2
Source dataset
uspto-grants-2007_01
Patent number
US07157487B2

Reaction notes

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