Acetic Acid → HCID 69301150, compound

HRID 2218123Notes

Reaction equation

HRID 2218123 reaction equation
C(O)(=O)C.[CH2:5]([O:7][C:8](=[O:35])[CH2:9][CH2:10][C:11]1[CH:16]=[CH:15][C:14]([CH2:17][N:18]2[CH:23]=[C:22]([Cl:24])[CH:21]=[C:20]([C:25]3[CH:30]=[CH:29][C:28]([N+:31]([O-])=O)=[CH:27][CH:26]=3)[C:19]2=[O:34])=[CH:13][CH:12]=1)[CH3:6]>C(O)C.O.[Fe]>[CH2:5]([O:7][C:8](=[O:35])[CH2:9][CH2:10][C:11]1[CH:12]=[CH:13][C:14]([CH2:17][N:18]2[CH:23]=[C:22]([Cl:24])[CH:21]=[C:20]([C:25]3[CH:30]=[CH:29][C:28]([NH2:31])=[CH:27][CH:26]=3)[C:19]2=[O:34])=[CH:15][CH:16]=1)[CH3:6]

Participants

6

Reactant 2

HCID 176Acetic AcidHCID 69300079HCID 69300079, compound

Product 1

HCID 69301150HCID 69301150, compound

Reagents, catalysts & solvents 3

HCID 23925IronCatalystHCID 702EthanolSolventHCID 962WaterSolvent

Procedure

Acetic acid (1 mL) followed by iron (160 mg, 2.9 mmol) were added to a solution of 3-(4-[5-chloro-3-(4-nitrophenyl)-2-oxo-2H-pyridin-1-ylmethyl]phenyl}-propionic acid ethyl ester (0.31 g, 0.72 mmol) in ethanol (10 mL) and water (5 mL) with stirring. The mixture was then heated at reflux for 2 hours and allowed to cool to room temperature. After basification with aqueous ammonia the mixture was filtered through a pad of celite (Diatomaceous Earth) and the filtrate evaporated to dryness. The residue was taken up in aqueous sodium bicarbonate/ethyl acetate and the organic layer washed with brine, dried over anhydrous sodium sulfate, filtered and evaporated to dryness. After purification by chromatography on silica gel with a gradient of 30-50% ethyl acetate in hexane the title compound was obtained as an oil.

Workup

  1. temperatureThe mixture was then heated
  2. temperatureat reflux for 2 hours
  3. filtrationAfter basification with aqueous ammonia the mixture was filtered through a pad of celite (Diatomaceous Earth)
  4. customthe filtrate evaporated to dryness
  5. washthe organic layer washed with brine
  6. dry with materialdried over anhydrous sodium sulfate
  7. filtrationfiltered
  8. customevaporated to dryness
  9. customAfter purification by chromatography on silica gel with a gradient of 30-50% ethyl acetate in hexane the title compound
  10. customwas obtained as an oil

Sources & evidence

ORD record
ord-7ee2f3de5c254024b464d39d85f9ec14
Source dataset
uspto-grants-2008_08
Patent number
US07410984B2

Reaction notes

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