Aluminum(III) Chloride → 4-chloro-5-(4-chlorophenyl)-2H-pyridazin-3-one

HRID 2224268Notes

Reaction equation

HRID 2224268 reaction equation
C([N:8]1[C:13](=[O:14])[C:12]([Cl:15])=[C:11]([C:16]2[CH:21]=[CH:20][C:19]([Cl:22])=[CH:18][CH:17]=2)[CH:10]=[N:9]1)C1C=CC=CC=1.[Cl-].[Al+3].[Cl-].[Cl-]>C1(C)C=CC=CC=1>[Cl:15][C:12]1[C:13](=[O:14])[NH:8][N:9]=[CH:10][C:11]=1[C:16]1[CH:17]=[CH:18][C:19]([Cl:22])=[CH:20][CH:21]=1

Participants

4

Reactant 2

HCID 6451240Aluminum(III) ChlorideHCID 597166542-benzyl-4-chloro-5-(4-chlorophenyl)pyridazin-3(2H)-one

Product 1

HCID 597167804-chloro-5-(4-chlorophenyl)-2H-pyridazin-3-oneYield 100.2%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
50 °C

Procedure

2-Benzyl-4-Chloro-5-(4-chloro-phenyl)-2H-pyridazin-3-one (3.19 g, 9.65 mmol) was dissolved in toluene (50 mL). Aluminum chloride (AlCl3, 3.22 g, 24.1 mmol) was then added and the reaction mixture was heated at 50° C. After 20 min, the reaction mixture was cooled to RT and then poured into ice-water (200 mL). The resultant solution was extracted with EtOAc (3×200 mL). The combined organic layers were washed with water (500 mL). The organic layer was dried (MgSO4), filtered and concentrated under reduced pressure. The residue was purified by column chromatography on silica gel using EtOAc to give the title compound, 4-chloro-5-(4-chlorophenyl)-2H-pyridazin-3-one (2.33 g) as a white solid. HPLC: 2.74 min.

Workup

  1. temperaturethe reaction mixture was cooled to RT
  2. extractionThe resultant solution was extracted with EtOAc (3×200 mL)
  3. washThe combined organic layers were washed with water (500 mL)
  4. dry with materialThe organic layer was dried (MgSO4)
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure
  7. customThe residue was purified by column chromatography on silica gel

Sources & evidence

ORD record
ord-ff69ac71302b43918854a342e1e2632e
Source dataset
uspto-grants-2008_05
Patent number
US07378418B2

Reaction notes

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