Water → HCID 59716568, compound

HRID 2224259Notes

Reaction equation

HRID 2224259 reaction equation
C([N:8]1[C:13](=[O:14])[C:12]([C:15]2[CH:20]=[CH:19][N:18]=[CH:17][CH:16]=2)=[C:11]([C:21]2[CH:26]=[CH:25][C:24]([F:27])=[CH:23][CH:22]=2)[CH:10]=[N:9]1)C1C=CC=CC=1.[Cl-].[Al+3].[Cl-].[Cl-].O>C1(C)C=CC=CC=1>[F:27][C:24]1[CH:23]=[CH:22][C:21]([C:11]2[CH:10]=[N:9][NH:8][C:13](=[O:14])[C:12]=2[C:15]2[CH:16]=[CH:17][N:18]=[CH:19][CH:20]=2)=[CH:26][CH:25]=1

Participants

5

Reactant 3

HCID 962WaterHCID 6451240Aluminum(III) ChlorideHCID 59716558HCID 59716558, compound

Product 1

HCID 59716568HCID 59716568, compoundYield 72%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
90 °C

Procedure

To a solution of 2-benzyl-5-(4-fluorophenyl)-4-(pyridin-4-yl)pyridazin-3(2H)-one (1.04 g, 2.91 mmol) in toluene (15 mL) was added aluminum chloride (970 mg, 7.28 mmol). The reaction was stirred at 90° C. for 30 min. After cooling to RT, the reaction mixture was poured into water (50 mL). The resulting mixture was extracted with EtOAc (3×50 mL). The combined organic layers were washed with saturated aqueous NaHCO3, saturated aqueous NaCl. The organic layer was dried (Na2SO4), filtered and concentrated. The resulting residue was triturated with EtOAc-hexane to give the title compound, 5-(4-fluorophenyl)-4-(pyridin-4-yl)pyridazin-3(2H)-one as an off-white solid (560 mg, 70%). LC/MS (method A): RT=1.25 min, (M+H)+=268.

Workup

  1. temperatureAfter cooling to RT
  2. extractionThe resulting mixture was extracted with EtOAc (3×50 mL)
  3. washThe combined organic layers were washed with saturated aqueous NaHCO3, saturated aqueous NaCl
  4. dry with materialThe organic layer was dried (Na2SO4)
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customThe resulting residue was triturated with EtOAc-hexane

Sources & evidence

ORD record
ord-cb005e71954e495fbf2e1bf6483774f3
Source dataset
uspto-grants-2008_05
Patent number
US07378418B2

Reaction notes

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