Phenylhydrazine → HCID 58072293, compound

HRID 1895253Notes

Reaction equation

HRID 1895253 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([N:8]2[CH:13]=[CH:12][C:11](=[O:14])[C:10]([C:15](=O)[CH:16]=[CH:17][N:18](C)C)=[N:9]2)[CH:5]=[CH:6][CH:7]=1.[C:22]1([NH:28]N)[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1>CO>[Cl:1][C:2]1[CH:3]=[C:4]([N:8]2[CH:13]=[CH:12][C:11](=[O:14])[C:10]([C:15]3[N:28]([C:22]4[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=4)[N:18]=[CH:17][CH:16]=3)=[N:9]2)[CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 7516PhenylhydrazineHCID 66710725HCID 66710725, compound

Product 1

HCID 58072293HCID 58072293, compoundYield 19%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of 1-(3-chlorophenyl)-3-[3-(dimethylamino)prop-2-enoyl]pyridazin-4(1H)-one (crude 573 mg, 1.89 mmol) in 20 mL of methanol was added phenylhydrazine (306 mg, 2.84 mmol). The mixture was refluxed for 4 h and concentrated. The residue was dissolved in dichloromethane (20 mL), washed with 1N HCl aqueous solution and brine, dried over Na2SO4, and concentrated under reduced pressure. The residue was purified by prep-HPLC to give 1-(3-chlorophenyl)-3-(1-phenyl-1H-pyrazol-5-yl)pyridazin-4(1H)-one (125 mg, 19% for two steps) as a yellow solid.

Workup

  1. temperatureThe mixture was refluxed for 4 h
  2. concentrationconcentrated
  3. dissolutionThe residue was dissolved in dichloromethane (20 mL)
  4. washwashed with 1N HCl aqueous solution and brine
  5. dry with materialdried over Na2SO4
  6. concentrationconcentrated under reduced pressure
  7. customThe residue was purified by prep-HPLC

Sources & evidence

ORD record
ord-5f237f01202f42e5a81b3385a8f0d012
Source dataset
uspto-grants-2013_08
Patent number
US08513251B2

Reaction notes

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