Sodium Bicarbonate → Methyl 2-(3-(pyridin-4-yl)phenyl)benzo[d]oxazole-7-carboxylate

HRID 415303Notes

Reaction equation

HRID 415303 reaction equation
[OH:1][C:2]1[C:11]([NH:12][C:13](=O)[C:14]2[CH:19]=[CH:18][CH:17]=[C:16]([C:20]3[CH:25]=[CH:24][N:23]=[CH:22][CH:21]=3)[CH:15]=2)=[CH:10][CH:9]=[CH:8][C:3]=1[C:4]([O:6][CH3:7])=[O:5].C(=O)(O)[O-].[Na+]>C(O)(=O)CC>[N:23]1[CH:24]=[CH:25][C:20]([C:16]2[CH:15]=[C:14]([C:13]3[O:1][C:2]4[C:3]([C:4]([O:6][CH3:7])=[O:5])=[CH:8][CH:9]=[CH:10][C:11]=4[N:12]=3)[CH:19]=[CH:18][CH:17]=2)=[CH:21][CH:22]=1

Participants

4

Reactant 2

HCID 516892Sodium BicarbonateHCID 66620682Methyl 2-hydroxy-3-(3-(pyridin-4-yl)benzamido)benzoate

Product 1

HCID 66621012Methyl 2-(3-(pyridin-4-yl)phenyl)benzo[d]oxazole-7-carboxylateYield 28%

Reagents, catalysts & solvents 1

HCID 1032Propionic AcidSolvent

Procedure

A mixture of methyl 2-hydroxy-3-(3-(pyridin-4-yl)benzamido)benzoate (0.9 g, 5 mmol) of propionic acid (50 mL) was stirred at reflux for 3 days. Then the mixture was adjusted to pH=7 by sodium bicarbonate. The mixture was extracted with ethyl acetate. The organic phase was washed with saturated sodium bicarbonate, brine, dried with anhydrous sodium sulfate. The solvent was removed under reduced pressure. The crude products was purified by chromatography (petroleum ether/ethyl acetate=5:1). 240 mg of methyl 2-(3-(pyridin-4-yl)phenyl)benzo[d]oxazole-7-carboxylate as a solid was obtained. Yield 28%. LC-MS (ESI) m/z: 331 (M+1)+.

Workup

  1. temperatureat reflux for 3 days
  2. extractionThe mixture was extracted with ethyl acetate
  3. washThe organic phase was washed with saturated sodium bicarbonate, brine
  4. dry with materialdried with anhydrous sodium sulfate
  5. customThe solvent was removed under reduced pressure
  6. customThe crude products was purified by chromatography (petroleum ether/ethyl acetate=5:1)

Sources & evidence

ORD record
ord-03d041f85eec46d88a05affacfb0dfd6
Source dataset
uspto-grants-2012_01
Patent number
US08088760B2

Reaction notes

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