Water → 2-benzyl-4,5-dibromopyridazin-3(2H)-one

HRID 612399Notes

Reaction equation

HRID 612399 reaction equation
[C:1](O)(=O)/[C:2](=[C:4](\[CH:6]=[O:7])/[Br:5])/[Br:3].Cl.Cl.[CH2:12]([NH:19][NH2:20])[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1.O>C(O)C>[CH2:12]([N:19]1[C:6](=[O:7])[C:4]([Br:5])=[C:2]([Br:3])[CH:1]=[N:20]1)[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1

Participants

5

Reactant 3

HCID 962WaterHCID 146540Benzylhydrazine dihydrochlorideHCID 3033972Mucobromic Acid

Product 1

HCID 99026992-benzyl-4,5-dibromopyridazin-3(2H)-oneYield 54.4%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Alternatively, a suspension of mucobromic acid (80 g., 310 mmol.) and benzylhydrazine dihydrochloride (60 g., 310 mmol.) in ethanol was heated to reflux for 16 hours. It was cooled to r.t. and under vigourous stirring water (50 mL) was added. The suspension was cooled in an ice bath and then filtered. The solid was washed with 95% aqueous ethanol and air dried. It was swished in hexanes (200 mL) and diethyl ether (25 mL), filtered and air dried to yield the title compound(58 g.).

Workup

  1. temperaturewas heated
  2. temperatureto reflux for 16 hours
  3. additionwas added
  4. temperatureThe suspension was cooled in an ice bath
  5. filtrationfiltered
  6. washThe solid was washed with 95% aqueous ethanol and air
  7. customdried
  8. filtrationdiethyl ether (25 mL), filtered
  9. customair dried

Sources & evidence

ORD record
ord-21e0d7d408fb4ae98056a12957933a83
Source dataset
uspto-grants-1999_12
Patent number
US06004960

Reaction notes

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