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

HRID 1644205Notes

Reaction equation

HRID 1644205 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-63dd4e43c2694e54bf922c98c82e0118
Source dataset
uspto-grants-2012_02
Patent number
US08124604B2

Reaction notes

Loading…