Water → 5-chloro-4-(4-chlorophenyl)pyridazin-3(2H)-one

HRID 2224252Notes

Reaction equation

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

Participants

Conditions

Temperature: 50 °C

Procedure

To a solution of 2-benzyl-5-chloro-4-(4-chlorophenyl)pyridazin-3(2H)-one (10.2 gm, 30.8 mmol) in toluene (154 mL) was added aluminum chloride (10.3 g, 77 mmol). The mixture was stirred at 50° C. for 1 h. After this time, the solution was cooled to RT, and the reaction mixture was poured into water (200 mL). The reaction mixture was extracted with EtOAc (3×100 mL). The combined organic layers were washed with saturated NaCl. The organic layer was dried (Na2SO4), filtered and concentrated. The resulting residue was triturated with EtOAc-hexane to give the title compound, 5-chloro-4-(4-chlorophenyl)pyridazin-3(2H)-one as an off-white solid (6.8 g, 92%). LC/MS (method A): RT=2.91 min, (M+H)+=241;

Workup

temperatureAfter this time, the solution was cooled to RT
extractionThe reaction mixture was extracted with EtOAc (3×100 mL)
washThe combined organic layers were washed with saturated NaCl
dry with materialThe organic layer was dried (Na2SO4)
filtrationfiltered
concentrationconcentrated
customThe resulting residue was triturated with EtOAc-hexane

Sources & evidence

ORD record: ord-0289fc3f5caf4c4e948f0ca18408bb82
Source dataset: uspto-grants-2008_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07378418B2

Reaction notes

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