Aluminum(III) Chloride → 4-(5-(4-Chlorophenyl)-3-oxo-2,3-dihydropyridazin-4-yl)benzonitrile

HRID 1865833Notes

Reaction equation

HRID 1865833 reaction equation
C([N:8]1[C:13](=[O:14])[C:12]([C:15]2[CH:22]=[CH:21][C:18]([C:19]#[N:20])=[CH:17][CH:16]=2)=[C:11]([C:23]2[CH:28]=[CH:27][C:26]([Cl:29])=[CH:25][CH:24]=2)[CH:10]=[N:9]1)C1C=CC=CC=1.[Al+3].[Cl-].[Cl-].[Cl-]>C1(C)C=CC=CC=1>[Cl:29][C:26]1[CH:25]=[CH:24][C:23]([C:11]2[CH:10]=[N:9][NH:8][C:13](=[O:14])[C:12]=2[C:15]2[CH:16]=[CH:17][C:18]([C:19]#[N:20])=[CH:21][CH:22]=2)=[CH:28][CH:27]=1

Participants

4

Reactant 2

HCID 6451240Aluminum(III) ChlorideHCID 690251454-(2-Benzyl-5-(4-chlorophenyl)-3-oxo-2,3-dihydropyridazin-4-yl)benzonitrile

Product 1

HCID 671292894-(5-(4-Chlorophenyl)-3-oxo-2,3-dihydropyridazin-4-yl)benzonitrileYield 79%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
80 °C

Procedure

To the suspension of 4-(2-benzyl-5-(4-chlorophenyl)-3-oxo-2,3-dihydropyridazin-4-yl)benzonitrile (3.62 gm, 9.12 mmol) in toluene (50 ml) at rt under argon was added AlCl3 (3.65 gm, 27.4 mmol). The reaction was heated to 80° C. and stirred at this temperature for 4 hrs. After this time, the solution was cooled to rt and concentrated under reduced pressure. Ice water (100 ml) was added to the reaction residue and the resulting slurry was stirred for 20 min. The solution was then diluted with EtOAc and the layers were separated. The aqueous layer was extracted with EtOAc (2×50 ml). The combined organic layers were washed with 1N NaOH (50 ml). The organic layer was then slurried with MgSO4 to remove excess water, filtered and concentrated to give the crude product. The crude product was triturated with EtOAc/Hex to give 2.21 gm (79% yield) 4-(5-(4-chlorophenyl)-3-oxo-2,3-dihydropyridazin-4-yl)benzonitrile. HPLC retention time (method B) 3.22 min; LCMS (M+H)=308.0.

Workup

  1. temperatureAfter this time, the solution was cooled to rt
  2. concentrationconcentrated under reduced pressure
  3. additionIce water (100 ml) was added to the reaction residue
  4. stirringthe resulting slurry was stirred for 20 min
  5. additionThe solution was then diluted with EtOAc
  6. customthe layers were separated
  7. extractionThe aqueous layer was extracted with EtOAc (2×50 ml)
  8. washThe combined organic layers were washed with 1N NaOH (50 ml)
  9. customto remove excess water
  10. filtrationfiltered
  11. concentrationconcentrated
  12. customto give the crude product
  13. customThe crude product was triturated with EtOAc/Hex

Sources & evidence

ORD record
ord-dbccff946c434e58abb79b8a4f7c23ba
Source dataset
uspto-grants-2009_12
Patent number
US07629342B2

Reaction notes

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