Acetic Acid → HCID 22388007, compound

HRID 1072902Notes

Reaction equation

HRID 1072902 reaction equation
[Cl:1][C:2]1[CH:22]=[C:21]([N+:23]([O-])=O)[CH:20]=[CH:19][C:3]=1[CH2:4][N:5]1[C:9]2=[N:10][C:11]([C:14]([O:16][CH3:17])=[O:15])=[CH:12][CH:13]=[C:8]2[N:7]=[C:6]1[CH3:18].C(O)(=O)C>C(O)C>[NH2:23][C:21]1[CH:20]=[CH:19][C:3]([CH2:4][N:5]2[C:9]3=[N:10][C:11]([C:14]([O:16][CH3:17])=[O:15])=[CH:12][CH:13]=[C:8]3[N:7]=[C:6]2[CH3:18])=[C:2]([Cl:1])[CH:22]=1

Participants

4

Reactant 2

HCID 176Acetic Acid2×HCID 22388187HCID 22388187, compound

Product 1

HCID 22388007HCID 22388007, compoundYield 94.1%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Methyl 3-(2-chloro-4-nitrobenzyl)-2-methyl-3H-imidazo[4,5-b]pyridine-5-carboxylate (705 mg) was suspended in ethanol (6 ml), and reduced iron (437 mg) and acetic acid (1.01 ml) were added. The mixture was refluxed under heating for 2 hr. Then, reduced iron (218 mg) and acetic acid (1.01 ml) were further added, and the mixture was refluxed under heating for 1 hr. The reaction mixture was filtered through Celite, the insoluble matter was washed with ethanol and the filtrate was concentrated under reduced pressure. To the concentrate were added a saturated aqueous sodium hydrogencarbonate solution and ethyl acetate to make the aqueous layer alkaline. At this stage, part of the objective compound was precipitated. The precipitate was collected by filtration and the filtrate was partitioned. The organic layer was washed successively with a saturated aqueous sodium hydrogencarbonate solution and saturated brine, dried over anhydrous magnesium sulfate, and filtrated. The objective compound that precipitated during neutralization was dissolved in a mixed solvent of methanol/chloroform (1/4), and the mixture was filtrated. Both filtrates were combined and concentrated under reduced pressure to give the objective compound (608 mg) as a white powder.

Workup

  1. temperatureThe mixture was refluxed
  2. temperatureunder heating for 2 hr
  3. temperaturethe mixture was refluxed
  4. temperatureunder heating for 1 hr
  5. filtrationThe reaction mixture was filtered through Celite
  6. washthe insoluble matter was washed with ethanol
  7. concentrationthe filtrate was concentrated under reduced pressure
  8. additionTo the concentrate were added a saturated aqueous sodium hydrogencarbonate solution and ethyl acetate
  9. customAt this stage, part of the objective compound was precipitated
  10. filtrationThe precipitate was collected by filtration
  11. customthe filtrate was partitioned
  12. washThe organic layer was washed successively with a saturated aqueous sodium hydrogencarbonate solution and saturated brine
  13. dry with materialdried over anhydrous magnesium sulfate
  14. filtrationfiltrated
  15. customThe objective compound that precipitated during neutralization
  16. dissolutionwas dissolved in a mixed solvent of methanol/chloroform (1/4)
  17. filtrationthe mixture was filtrated
  18. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-2a97b553c00a4aa8b2a55908d691c127
Source dataset
uspto-grants-2005_06
Patent number
US06911469B2

Reaction notes

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