Hydrazine hydrate (1:1) → 6-phenyl-4,5-dihydro-3(2h)-pyridazinone

HRID 1995338Notes

Reaction equation

HRID 1995338 reaction equation
[C:1]([CH2:9][CH2:10][C:11]([OH:13])=O)(=O)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.O.[NH2:15][NH2:16]>C(O)C>[C:2]1([C:1]2[CH2:9][CH2:10][C:11](=[O:13])[NH:15][N:16]=2)[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 24654Hydrazine hydrate (1:1)HCID 728713-Benzoylpropionic acid

Product 1

HCID 2429356-phenyl-4,5-dihydro-3(2h)-pyridazinone

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of 3-benzoylpropionic acid (89 g), 80% hydrazine hydrate (25.5 ml) in ethanol (1000 ml) is refluxed for 6 hrs, cooled and filtered to give 75.6 g of 6-phenyl-4,5-dihydro-3(2H)-pyridazinone. Bromine (70 g) is added dropwise to a solution of the above pyridazinone in acetic acid (200 ml) at 80° C. After the addition is over, the mixture is heated to 100° C. for 15 minutes, cooled, filtered and washed with isopropyl ether. The solid is slurried in water, adjusted to pH 10 and filtered to give 60 g of the product 6-phenyl-3(2H)-pyridazinone.

Workup

  1. temperatureis refluxed for 6 hrs
  2. temperaturecooled
  3. filtrationfiltered

Sources & evidence

ORD record
ord-8234acaf50c94e5c9b69dfa7904cf8e0
Source dataset
uspto-grants-1983_09
Patent number
US04404203

Reaction notes

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