Sodium Bicarbonate → HCID 18667592, compound

HRID 1060011Notes

Reaction equation

HRID 1060011 reaction equation
C([O:3][C:4](=O)[CH:5]=[CH:6][C:7]1[CH:12]=[CH:11][C:10]([C:13]2[CH:18]=[C:17]([O:19][CH3:20])[CH:16]=[CH:15][N:14]=2)=[CH:9][C:8]=1[N+:21]([O-])=O)C.C(=O)([O-])O.[Na+]>C(O)(=O)C.[Fe]>[CH3:20][O:19][C:17]1[CH:16]=[CH:15][N:14]=[C:13]([C:10]2[CH:9]=[C:8]3[C:7]([CH:6]=[CH:5][C:4](=[O:3])[NH:21]3)=[CH:12][CH:11]=2)[CH:18]=1

Participants

5

Reactant 2

HCID 516892Sodium BicarbonateHCID 54291565HCID 54291565, compound

Product 1

HCID 18667592HCID 18667592, compoundYield 27.6%

Reagents, catalysts & solvents 2

HCID 23925IronCatalystHCID 176Acetic AcidSolvent

Conditions

Temperature
100 °C

Procedure

To a suspension of 4-(4-methoxypyridin-2-yl)-2-nitrocinnamic acid ethyl ester (659 mg) in acetic acid (11 ml) was added iron powder (673 mg), and the mixture was stirred at 100° C. for 2 hours. After cooling, the reaction mixture was poured into a saturated aqueous sodium hydrogencarbonate solution and filtered, and the filtrate was extracted with dichloromethane-methanol (5:1). The organic layer was washed with brine, dried over sodium sulfate and evaporated under reduced pressure. The residue was dissolved in ethanol (5 ml). To the solution was added a solution of sodium methoxide in methanol (28%, 3 ml), and the mixture was refluxed for 2 hours. After cooling, the reaction mixture was poured into a saturated aqueous ammonium chloride solution and extracted with dichloromethane. The organic layer was washed with brine, dried over sodium sulfate and evaporated under reduced pressure to give 7-(4-methoxypyridin-2-yl)-2-quinolone (140 mg).

Workup

  1. temperatureAfter cooling
  2. filtrationfiltered
  3. extractionthe filtrate was extracted with dichloromethane-methanol (5:1)
  4. washThe organic layer was washed with brine
  5. dry with materialdried over sodium sulfate
  6. customevaporated under reduced pressure
  7. dissolutionThe residue was dissolved in ethanol (5 ml)
  8. additionTo the solution was added a solution of sodium methoxide in methanol (28%, 3 ml)
  9. temperaturethe mixture was refluxed for 2 hours
  10. temperatureAfter cooling
  11. additionthe reaction mixture was poured into a saturated aqueous ammonium chloride solution
  12. extractionextracted with dichloromethane
  13. washThe organic layer was washed with brine
  14. dry with materialdried over sodium sulfate
  15. customevaporated under reduced pressure

Sources & evidence

ORD record
ord-c6a7154922864c809712f5905613620e
Source dataset
uspto-grants-2003_02
Patent number
US06521643B1

Reaction notes

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