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

HRID 68459

Reaction equation

HRID 68459 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-60a5d0ce5d514d2c817804be1c5d4df8
Source dataset
uspto-grants-2014_09
Patent number
US08822457B2

Linked notes

Loading…