Hydrazine hydrate (1:1) → 6-(4-methoxy-phenyl)-5-phenyl-4,5-dihydro-2H-pyridazin-3-one

HRID 887008Notes

Reaction equation

HRID 887008 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([C:9](=O)[CH:10]([C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)[CH2:11][C:12](O)=[O:13])=[CH:5][CH:4]=1.O.[NH2:23][NH2:24]>CCO>[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([C:9]2[CH:10]([C:15]3[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=3)[CH2:11][C:12](=[O:13])[NH:23][N:24]=2)=[CH:5][CH:4]=1

Participants

4

Reactant 2

HCID 24654Hydrazine hydrate (1:1)HCID 43613644-(4-Methoxyphenyl)-4-oxo-3-phenylbutanoic acid

Product 1

HCID 670099286-(4-methoxy-phenyl)-5-phenyl-4,5-dihydro-2H-pyridazin-3-oneYield 99%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution of 4-(4-methoxy-phenyl)-4-oxo-3-phenyl-butyric acid (1.5 g, 5.28 mmol) and hydrazine hydrate (1.5 eq., 363 μL) in 20 mL of EtOH was stirred at 80° C. overnight. The solvent was reduced and the solid was filtered and then washed with cold EtOH to give 6-(4-methoxy-phenyl)-5-phenyl-4,5-dihydro-2H-pyridazin-3-one (1.46 g, 99%): mp 176-7° C.; MS m/z 281 (M+H).

Workup

  1. filtrationthe solid was filtered
  2. washwashed with cold EtOH

Sources & evidence

ORD record
ord-6dea7abe00e04091abff3bf14d19932b
Source dataset
uspto-grants-2012_08
Patent number
US08247414B2

Reaction notes

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