Hydrazine, (phenylmethyl)-, hydrochloride (1:1) → 2-Benzyl-6-phenyl-4,5-dihydropyridazin-3(2H)-one

HRID 1747783Notes

Reaction equation

HRID 1747783 reaction equation
O=[C:2]([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)[CH2:3][CH2:4][C:5]([OH:7])=O.Cl.[CH2:15]([NH:22][NH2:23])[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1.C([O-])(=O)C.[Na+]>C(O)C>[CH2:15]([N:22]1[C:5](=[O:7])[CH2:4][CH2:3][C:2]([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)=[N:23]1)[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1

Participants

5

Reactant 3

HCID 14084Hydrazine, (phenylmethyl)-, hydrochloride (1:1)HCID 728713-Benzoylpropionic acidHCID 517045Sodium Acetate

Product 1

HCID 131632302-Benzyl-6-phenyl-4,5-dihydropyridazin-3(2H)-oneYield 12.1%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution of 4-oxo-4-phenylbutanoic acid (1.0 g) in ethanol (28 mL) were added benzylhydrazine hydrochloride (1.1 g) and sodium acetate (4.2 g) at room temperature, and the mixture was heated under reflux overnight. The solvent was evaporated under reduced pressure, saturated aqueous sodium hydrogen carbonate solution was added, and the mixture was extracted with ethyl acetate. The extract was dried over anhydrous sodium sulfate and concentrated under reduced pressure to give the title compound (0.18 g).

Workup

  1. temperaturethe mixture was heated
  2. temperatureunder reflux overnight
  3. customThe solvent was evaporated under reduced pressure, saturated aqueous sodium hydrogen carbonate solution
  4. additionwas added
  5. extractionthe mixture was extracted with ethyl acetate
  6. dry with materialThe extract was dried over anhydrous sodium sulfate
  7. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-d66fdbfac72042498fb38350eb557852
Source dataset
uspto-grants-2015_10
Patent number
US09150588B2

Reaction notes

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