Hydrochloric Acid → HCID 178418522, compound

HRID 3856Notes

Reaction equation

HRID 3856 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[C:7]([O:9][CH3:10])[CH:6]=[CH:5][C:4]=1[C:11]1[NH:12][C:13]2[C:14]([N:20]=1)=[N+:15]([O-])[CH:16]=[CH:17][CH:18]=2.Cl.[OH2:22]>C(OC(=O)C)(=O)C>[CH3:1][O:2][C:3]1[CH:8]=[C:7]([O:9][CH3:10])[CH:6]=[CH:5][C:4]=1[C:11]1[N:20]=[C:14]2[NH:15][C:16](=[O:22])[CH2:17][CH:18]=[C:13]2[N:12]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 962WaterHCID 178418550HCID 178418550, compound

Product 1

HCID 178418522HCID 178418522, compound

Reagents, catalysts & solvents 1

HCID 7918Acetic AnhydrideSolvent

Conditions

Temperature
120 °C

Procedure

Four grams of 2-(2,4-dimethoxy-phenyl)-imidazo[4,5-b]pyridin-4-oxide is suspended in 40 ml of acetic anhydride and refluxed for 2.75 hours. After cooling the mixture is poured onto 150 ml of ice, 25 ml of 6N hydrochloric acid are added, and the mixture is stirred at 120° C. for 30 minutes. It is cooled to ambient temperature, 50 ml of water are added, and the precipitate is subjected to suction filtration. The product is purified by chromatography on silica gel [eluant: methylene chloride/methanol (100:0 to 100:10)].

Workup

  1. temperaturerefluxed for 2.75 hours
  2. temperatureAfter cooling the mixture
  3. additionare added
  4. temperatureIt is cooled to ambient temperature
  5. filtrationthe precipitate is subjected to suction filtration
  6. customThe product is purified by chromatography on silica gel [eluant: methylene chloride/methanol (100:0 to 100:10)]

Sources & evidence

ORD record
ord-eed20875f89042a78eaca70db7681c77
Source dataset
uspto-grants-1988_02
Patent number
US04722929

Reaction notes

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