3-Pyridinecarboxaldehyde → Methyl (2-(3-pyridyl)-6-benzoxazolyl)acetate

HRID 1372746Notes

Reaction equation

HRID 1372746 reaction equation
[N:1]1[CH:6]=[CH:5][CH:4]=[C:3]([CH:7]=[O:8])[CH:2]=1.[NH2:9][C:10]1[CH:15]=[CH:14][C:13]([CH2:16][C:17]([O:19][CH3:20])=[O:18])=[CH:12][C:11]=1O.C(O)(=O)C.C(O)(=O)C.IC1C=CC=CC=1>CCO>[N:1]1[CH:6]=[CH:5][CH:4]=[C:3]([C:7]2[O:8][C:11]3[CH:12]=[C:13]([CH2:16][C:17]([O:19][CH3:20])=[O:18])[CH:14]=[CH:15][C:10]=3[N:9]=2)[CH:2]=1

Participants

5

Reactant 3

HCID 103713-PyridinecarboxaldehydeHCID 12217721Iodo benzene diacetateHCID 17858854Methyl 2-(4-amino-3-hydroxyphenyl)acetate

Product 1

HCID 58778369Methyl (2-(3-pyridyl)-6-benzoxazolyl)acetateYield 23%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

In EtOH (15 ml), pyridine-3-aldehyde (0.63 g, 5.89 mmol) and methyl 4-amino-3-hydroxyphenylacetate (1.06 g, 5.85 mmol) were stirred at room temperature for 20 hours. To the reaction mixture was added iodobenzene diacetate (2.26 g, 7.02 mmol), followed by stirring at room temperature for 20 minutes. The reaction mixture was distilled under reduced pressure to remove the solvent and the residue was dissolved in ethyl acetate. The ethyl acetate solution was washed with a saturated aqueous solution of sodium bicarbonate, dried over anhydrous sodium sulfate, and distilled under reduced pressure to remove the solvent. The residue was purified by chromatography on a silica gel column, whereby from n-hexane/ethyl acetate (1:1, v/v) eluate fractions, methyl (2-(3-pyridyl)-6-benzoxazolyl)acetate (360 mg, 23%) was obtained as a pale yellow solid.

Workup

  1. distillationThe reaction mixture was distilled under reduced pressure
  2. customto remove the solvent
  3. dissolutionthe residue was dissolved in ethyl acetate
  4. washThe ethyl acetate solution was washed with a saturated aqueous solution of sodium bicarbonate
  5. dry with materialdried over anhydrous sodium sulfate
  6. distillationdistilled under reduced pressure
  7. customto remove the solvent
  8. customThe residue was purified by chromatography on a silica gel column, whereby from n-hexane/ethyl acetate (1:1

Sources & evidence

ORD record
ord-1ce7525607b7446abc84ffd12e0ba13c
Source dataset
uspto-grants-2007_01
Patent number
US07157487B2

Reaction notes

Loading…