Phenylhydrazine → 4,5-Dichloro-2-phenyl-3(2H)-pyridazinone

HRID 2427791Notes

Reaction equation

HRID 2427791 reaction equation
[C:1]([OH:9])(=O)/[C:2](=[C:4](\[CH:6]=O)/[Cl:5])/[Cl:3].[C:10]1([NH:16][NH2:17])[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1>C(O)C>[Cl:3][C:2]1[C:1](=[O:9])[N:16]([C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)[N:17]=[CH:6][C:4]=1[Cl:5]

Participants

4

Reactant 2

HCID 7516PhenylhydrazineHCID 2771871Mucochloric Acid

Product 1

HCID 728134,5-Dichloro-2-phenyl-3(2H)-pyridazinone

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Mucochloric acid (9.3 g, 0.055 moles) was dissolved in ethanol (60 ml) and phenyl hydrazine (5.4 g, 0.05 moles) was added. The reaction mixture was stirred at room temperature for 2 hours. Evaporated to a low bulk and the residue was suspended in glacial acetic acid (60 ml). Refluxed with stirring for 3 hours. Evaporated to dryness and triturated with methanol to give the required product as a pale brown solid. (11.0 g, 91%)

Workup

  1. customEvaporated to a low bulk
  2. temperatureRefluxed
  3. stirringwith stirring for 3 hours
  4. customEvaporated to dryness
  5. customtriturated with methanol

Sources & evidence

ORD record
ord-8270f2bcecc446f6830a59e0d0aa862c
Source dataset
uspto-grants-2011_06
Patent number
US07968711B2

Reaction notes

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