6-[(2-Fluorophenyl)methyl]-3(2H)-pyridazinone → 6-[3-(2,4,6-trichlorobenzoyl)-6-fluorobenzyl)-2H-pyridazin-3-one

HRID 1419498Notes

Reaction equation

HRID 1419498 reaction equation
[Al+3].[Cl-].[Cl-].[Cl-].[F:5][C:6]1[CH:19]=[CH:18][CH:17]=[CH:16][C:7]=1[CH2:8][C:9]1[CH:10]=[CH:11][C:12](=[O:15])[NH:13][N:14]=1.[Cl:20][C:21]1[CH:29]=[C:28]([Cl:30])[CH:27]=[C:26]([Cl:31])[C:22]=1[C:23](Cl)=[O:24].C(Cl)(=O)C(Cl)=O.C(Cl)Cl>C(Cl)Cl.CN(C=O)C>[Cl:20][C:21]1[CH:29]=[C:28]([Cl:30])[CH:27]=[C:26]([Cl:31])[C:22]=1[C:23]([C:17]1[CH:16]=[C:7]([C:6]([F:5])=[CH:19][CH:18]=1)[CH2:8][C:9]1[CH:10]=[CH:11][C:12](=[O:15])[NH:13][N:14]=1)=[O:24]

Participants

7

Reactant 4

HCID 14805366-[(2-Fluorophenyl)methyl]-3(2H)-pyridazinoneHCID 27337032,4,6-Trichlorobenzoyl chlorideHCID 6451240Aluminum(III) ChlorideHCID 21906498HCID 21906498, compound

Product 1

HCID 543549036-[3-(2,4,6-trichlorobenzoyl)-6-fluorobenzyl)-2H-pyridazin-3-one

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 6344DichloromethaneSolvent

Procedure

AlCl3 (1.75 g, 13.1 mmol) was added to a solution of 6-(2-fluorobenzyl)-2H-pyridazin-3-one (0.9 g, 4.4 mmol) [prepared as described above] in methylene chloride (20 ml) at ambient temperature and under a nitrogen atmosphere. 2,4,6-trichlorobenzoyl chloride [(1.98 g, 8.78 mmol) prepared from the corresponding acid by treatment with oxalyl chloride/ methylene chloride with a trace of DMF] was added to the slurry. After stirring overnight, the reaction was quenched with ice. The product was extracted into ethyl acetate, and dried over MgSO4. The solvent was removed in vacuo and the crude product was chromatographed on a silica gel column (ether) to give impure 6-[3-(2,4,6-trichlorobenzoyl)-6-fluorobenzyl)-2H-pyridazin-3-one (0.43 g). Recrystallization from acetone/hexanes mixture gave pure 6-[3-(2,4,6-trichlorobenzoyl)-6-fluorobenzyl)-2H-pyridazin-3-one (0.34 g, 18% yield) as a solid, mp 185.0°-185.3° C.

Workup

  1. additionwas added to the slurry
  2. customthe reaction was quenched with ice
  3. extractionThe product was extracted into ethyl acetate
  4. dry with materialdried over MgSO4
  5. customThe solvent was removed in vacuo
  6. customthe crude product was chromatographed on a silica gel column (ether)

Sources & evidence

ORD record
ord-62604a8fcbce4deaa6012287b1433ede
Source dataset
uspto-grants-1999_03
Patent number
US05886178

Reaction notes

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