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

HRID 2224238Notes

Reaction equation

HRID 2224238 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]([Cl:27])=[CH:23][CH:22]=2)[CH:10]=[N:9]1)C1C=CC=CC=1.[Al+3].[Cl-].[Cl-].[Cl-]>C1(C)C=CC=CC=1>[Cl: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

4

Reactant 2

HCID 6451240Aluminum(III) ChlorideHCID 597169102-benzyl-5-(4-chlorophenyl)-4-(pyridin-4-yl)pyridazin-3(2H)-one

Product 1

HCID 597167155-(4-chlorophenyl)-4-(pyridin-4-yl)pyridazin-3(2H)-oneYield 96%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

To a solution of 2-benzyl-5-(4-chlorophenyl)-4-(pyridin-4-yl)pyridazin-3(2H)-one (7.0 g, 18.73 mmol) in toluene (50 mL) in a round bottomed flask was added AlCl3 (7.5 g, 56.25 mmol) under a stream of argon. The flask was placed in an oil bath preheated at 80° C. After 2 hours, the reaction mixture was cooled to RT and then poured into crushed ice (200 g). The precipitate formed was collected by filtration, washed with water (2×50 mL) followed by ether (50 mL) and dried in a vacuum oven at 40° C. to give the title compound, 5-(4-chlorophenyl)-4-(pyridin-4-yl)pyridazin-3(2H)-one (5.1 g, 96%) as a white solid. HPLC: 1.37 min; MS, M+H=284.

Workup

  1. customThe flask was placed in an oil bath
  2. custompreheated at 80° C
  3. additionpoured
  4. customThe precipitate formed
  5. filtrationwas collected by filtration
  6. washwashed with water (2×50 mL)
  7. customdried in a vacuum oven at 40° C.

Sources & evidence

ORD record
ord-88f3bd64157344328b81e1bd362b4fbc
Source dataset
uspto-grants-2008_05
Patent number
US07378418B2

Reaction notes

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