Hydrochloric Acid → (2-(3-Pyridyl)-6-benzoxazolyl)acetic acid

HRID 1372747Notes

Reaction equation

HRID 1372747 reaction equation
[N:1]1[CH:6]=[CH:5][CH:4]=[C:3]([C:7]2[O:8][C:9]3[CH:15]=[C:14]([CH2:16][C:17]([O:19]C)=[O:18])[CH:13]=[CH:12][C:10]=3[N:11]=2)[CH:2]=1.C1COCC1.[OH-].[Na+].Cl>O>[N:1]1[CH:6]=[CH:5][CH:4]=[C:3]([C:7]2[O:8][C:9]3[CH:15]=[C:14]([CH2:16][C:17]([OH:19])=[O:18])[CH:13]=[CH:12][C:10]=3[N:11]=2)[CH:2]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 8028TetrahydrofuranHCID 14798Sodium HydroxideHCID 58778369Methyl (2-(3-pyridyl)-6-benzoxazolyl)acetate

Product 1

HCID 17859071(2-(3-Pyridyl)-6-benzoxazolyl)acetic acidYield 52.5%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To methyl (2-(3-pyridyl)-6-benzoxazolyl)acetate (360 mg, 1.34 mmol) were added THF (8 ml) and 0.5N NaOH (8.0 ml, 4.00 mmol). The resulting mixture was stirred at room temperature for 20 hours. To the reaction mixture were added water and 1N HCl (5.0 ml, 5 mmol) to acidify the mixture, followed by extraction with ethyl acetate. The extract was washed with saturated brine, dried over anhydrous sodium sulfate, and distilled under reduced pressure to remove the solvent to give (2-(3-pyridyl)-6-benzoxazolyl)acetic acid (179 mg, 52%) as a yellow solid.

Workup

  1. extractionfollowed by extraction with ethyl acetate
  2. washThe extract was washed with saturated brine
  3. dry with materialdried over anhydrous sodium sulfate
  4. distillationdistilled under reduced pressure
  5. customto remove the solvent

Sources & evidence

ORD record
ord-b9fa33eb46a440228b4097b5d08e8561
Source dataset
uspto-grants-2007_01
Patent number
US07157487B2

Reaction notes

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