Acetic Acid → 4,6-Dichloropyridazin-3(2H)-one

HRID 600362Notes

Reaction equation

HRID 600362 reaction equation
Cl[C:2]1[N:3]=[N:4][C:5]([Cl:9])=[CH:6][C:7]=1[Cl:8].C(O)(=[O:12])C>>[Cl:8][C:7]1[C:2](=[O:12])[NH:3][N:4]=[C:5]([Cl:9])[CH:6]=1

Participants

3

Reactant 2

HCID 176Acetic AcidHCID 951233,4,6-Trichloropyridazine

Product 1

HCID 580162054,6-Dichloropyridazin-3(2H)-one

Procedure

3,4,6-Trichloro-pyridazine (34.39 g, 187.5 mmol) in 100 mL acetic acid was heated at reflux for three hours. The resulting mixture was cooled to room temperature and filtered. The filtrate was diluted with ethylacetate. This was washed three times with water, washed with brine, dried over anhydrous MgSO4, concentrated in vacuo, and purified by flash chromatography (30% ethylacetate/hexanes) to yield 4,6-Dichloro-2H-pyridazin-3-one (6.143 g, 37.23 mmol). MS (ESI) 165.0 (M+H)+.

Workup

  1. temperatureat reflux for three hours
  2. filtrationfiltered
  3. additionThe filtrate was diluted with ethylacetate
  4. washThis was washed three times with water
  5. washwashed with brine
  6. dry with materialdried over anhydrous MgSO4
  7. concentrationconcentrated in vacuo
  8. custompurified by flash chromatography (30% ethylacetate/hexanes)

Sources & evidence

ORD record
ord-f743a4b002054f1ba87b2b692249b1f9
Source dataset
uspto-grants-2011_03
Patent number
US07902194B2

Reaction notes

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