Sodium Bicarbonate → HCID 66620461, compound

HRID 415286Notes

Reaction equation

HRID 415286 reaction equation
O[C:2]1[C:11]([NH:12][C:13](=[O:26])[C:14]2[CH:19]=[CH:18][C:17]([C:20]3[CH:25]=[CH:24][N:23]=[CH:22][CH:21]=3)=[CH:16][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:17]2[CH:16]=[CH:15][C:14]([C:13]3[O:26][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]=2)=[CH:21][CH:22]=1

Participants

4

Reactant 2

HCID 516892Sodium BicarbonateHCID 66621507HCID 66621507, compound

Product 1

HCID 66620461HCID 66620461, compoundYield 16.1%

Reagents, catalysts & solvents 1

HCID 1032Propionic AcidSolvent

Procedure

A mixture of methyl 2-hydroxy-3-(4-(pyridin-4-yl)benzamido)benzoate (1.04 g, 3 mmol) in 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=20:1 to 5:1). 160 mg of methyl 2-(4-(pyridin-4-yl)phenyl)benzo[d]oxazole-7-carboxylate as a solid was obtained. Yield: 16%. 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=20:1 to 5:1)

Sources & evidence

ORD record
ord-acd0af4609fa4144928678882b554a65
Source dataset
uspto-grants-2012_01
Patent number
US08088760B2

Reaction notes

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