Acetic Acid → HCID 22024500, compound

HRID 501018Notes

Reaction equation

HRID 501018 reaction equation
[Cl:1][C:2]1[CH:7]=[C:6]([Cl:8])[CH:5]=[CH:4][C:3]=1[C:9]1[C:10]2[N:11]([C:15]([N+:19]([O-])=O)=[C:16]([CH3:18])[N:17]=2)[CH:12]=[CH:13][N:14]=1.C(O)(=O)C>C(O)C.[Fe]>[Cl:1][C:2]1[CH:7]=[C:6]([Cl:8])[CH:5]=[CH:4][C:3]=1[C:9]1[C:10]2[N:11]([C:15]([NH2:19])=[C:16]([CH3:18])[N:17]=2)[CH:12]=[CH:13][N:14]=1

Participants

5

Reactant 2

HCID 176Acetic AcidHCID 22024556HCID 22024556, compound

Product 1

HCID 22024500HCID 22024500, compoundYield 35.4%

Reagents, catalysts & solvents 2

HCID 23925IronCatalystHCID 702EthanolSolvent

Procedure

8-(2,4-Dichlorophenyl)-2-methyl-3-nitroimidazo[1,2-a]pyrazine (25 mg, 0.077 mmol) was dissolved in ethanol (0.36 mL), then acetic acid (0.5 mL) and iron powders (22 mg) were added thereto, and the mixture was stirred for 1 hour by heating under reflux. After the reaction mixture was allowed to cool, the solvent was evaporated and it was extracted with ethyl acetate. The organic layer was dried over anhydrous magnesium sulfate and evaporated. The resulting residue was purified by silica gel column chromatography (ethyl acetate:n-hexane=4:1) to give 8-(2,4-dichlorophenyl)-2-methylimidazo[1,2-a]pyrazin-3-amine (8 mg) as yellow crystals.

Workup

  1. temperatureby heating
  2. temperatureunder reflux
  3. temperatureto cool
  4. customthe solvent was evaporated
  5. extractionit was extracted with ethyl acetate
  6. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  7. customevaporated
  8. customThe resulting residue was purified by silica gel column chromatography (ethyl acetate:n-hexane=4:1)

Sources & evidence

ORD record
ord-da4751e33b6747bb81ca648fa806897f
Source dataset
uspto-grants-2010_08
Patent number
US07772249B2

Reaction notes

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