Sodium Acetate → 6-[(2-Fluorophenyl)methyl]-3(2H)-pyridazinone

HRID 1419497Notes

Reaction equation

HRID 1419497 reaction equation
[F:1][C:2]1[CH:15]=[CH:14][CH:13]=[CH:12][C:3]=1[CH2:4][C:5]1[N:10]=[N:9][C:8](Cl)=[CH:7][CH:6]=1.C([O-])(=[O:18])C.[Na+]>C(O)(=O)C.O>[F:1][C:2]1[CH:15]=[CH:14][CH:13]=[CH:12][C:3]=1[CH2:4][C:5]1[CH:6]=[CH:7][C:8](=[O:18])[NH:9][N:10]=1

Participants

5

Reactant 2

HCID 517045Sodium AcetateHCID 64045713-Chloro-6-(2-fluorobenzyl)pyridazine

Product 1

HCID 14805366-[(2-Fluorophenyl)methyl]-3(2H)-pyridazinoneYield 65.6%

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 962WaterSolvent

Conditions

Temperature
110 °C

Procedure

6-(2-Fluorobenzyl)-3-chloropyridazine (2.5 g, 11.2 mmol) [prepared as described above] was dissolved in acetic acid (15 ml). Sodium acetate (3.37 g, 24.8 mmol) was added and the reaction mixture was heated at 110° C. under a nitrogen atmosphere. After 1.5 h the reaction mixture was diluted with water and the product was extracted into ethyl acetate. The organic extracts were washed with water, aqueous NaHCO3 and brine, and dried over MgSO4. The solvent was removed in vacuo and the crude product was chromatographed on a silica gel column (50% ethyl acetate in hexanes) to give 6-(2-fluorobenzyl)-2H-pyridazin-3-one (1.5 g, 55% yield) as a yellow solid.

Workup

  1. extractionthe product was extracted into ethyl acetate
  2. washThe organic extracts were washed with water, aqueous NaHCO3 and brine
  3. dry with materialdried over MgSO4
  4. customThe solvent was removed in vacuo
  5. customthe crude product was chromatographed on a silica gel column (50% ethyl acetate in hexanes)

Sources & evidence

ORD record
ord-f854fbd3e1254b6bb87ecf2f3311a003
Source dataset
uspto-grants-1999_03
Patent number
US05886178

Reaction notes

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