Aluminum(III) Chloride → HCID 21453475, compound

HRID 1430609Notes

Reaction equation

HRID 1430609 reaction equation
C([N:8]1[C:13](=[O:14])[CH:12]=[C:11]([C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)[C:10]([Cl:21])=[N:9]1)C1C=CC=CC=1.[Cl-].[Al+3].[Cl-].[Cl-]>C1(C)C=CC=CC=1>[Cl:21][C:10]1[C:11]([C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)=[CH:12][C:13](=[O:14])[NH:8][N:9]=1

Participants

4

Reactant 2

HCID 6451240Aluminum(III) ChlorideHCID 67422807HCID 67422807, compound

Product 1

HCID 21453475HCID 21453475, compoundYield 83.9%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

To a solution of 2-benzyl-6-chloro-5-phenylpyridazin-3(2H)-one (1.45 g, 4.89 mmol) in toluene (15 mL) under argon at 90° C. was added aluminum chloride (1.629 g, 12.22 mmol) and the reaction was stirred for 20 min. It was then allowed to cool to room temperature and quenched with water, extracted with EtOAc, dried over MgSO4 and concentrated. The residue was purified by preparative HPLC to give the title compound as a white solid (847.6 mg). LCMS m/z=207 [M+H]+; 1H NMR (400 MHz, CDCl3) δ ppm 6.97 (s, 1H), 7.41-7.54 (m, 5H).

Workup

  1. customquenched with water
  2. extractionextracted with EtOAc
  3. dry with materialdried over MgSO4
  4. concentrationconcentrated
  5. customThe residue was purified by preparative HPLC

Sources & evidence

ORD record
ord-6fe8c2b0897c477b86a140d148c3b3ef
Source dataset
uspto-grants-2015_01
Patent number
US08940891B2

Reaction notes

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