Acetic Anhydride → N-[3-(1,6-Dihydro-6-oxo-3-pyridazinyl)phenyl]acetamide

HRID 35625Notes

Reaction equation

HRID 35625 reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]([C:8]2[CH:9]=[CH:10][C:11](=[O:14])[NH:12][N:13]=2)[CH:5]=[CH:6][CH:7]=1.[C:15](OC(=O)C)(=[O:17])[CH3:16]>>[O:14]=[C:11]1[NH:12][N:13]=[C:8]([C:4]2[CH:3]=[C:2]([NH:1][C:15](=[O:17])[CH3:16])[CH:7]=[CH:6][CH:5]=2)[CH:9]=[CH:10]1

Participants

3

Reactant 2

HCID 7918Acetic AnhydrideHCID 113444556-(3-Aminophenyl)-2,3-dihydropyridazin-3-one

Product 1

HCID 15595699N-[3-(1,6-Dihydro-6-oxo-3-pyridazinyl)phenyl]acetamide

Procedure

A mixture of 37 g of 6-(3-aminophenyl)-3(2H)-pyridazinone and 500 ml of acetic anhydride was heated at 85°-90° C. for 8 hours. The solvent was removed in vacuo and the residue dissolved in 500 ml of methanol. To this solution was added portionwise 40 g of potassium hydroxide. The solution was refluxed for 3 hours and the solvent removed in vacuo. The residue was dissolved in water and the solution neutralized with hydrochloric acid. The resulting solid was collected and recrystallized from dichloromethane-methanol, giving 10.8 g of the desired compound as crystals, mp 250°-252° C. (dec.).

Workup

  1. temperaturewas heated at 85°-90° C. for 8 hours
  2. customThe solvent was removed in vacuo
  3. dissolutionthe residue dissolved in 500 ml of methanol
  4. additionTo this solution was added portionwise 40 g of potassium hydroxide
  5. temperatureThe solution was refluxed for 3 hours
  6. customthe solvent removed in vacuo
  7. dissolutionThe residue was dissolved in water
  8. customThe resulting solid was collected
  9. customrecrystallized from dichloromethane-methanol

Sources & evidence

ORD record
ord-4693b9de569d4a6cbf62c8ff01cdb088
Source dataset
uspto-grants-1988_08
Patent number
US04767765

Reaction notes

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