Methanol → 3(2H)-Pyridazinone, 2-(2-hydroxyethyl)-6-phenyl-

HRID 2227245Notes

Reaction equation

HRID 2227245 reaction equation
[K].[C:2]1([C:8]2[CH:9]=[CH:10][C:11](=[O:14])[NH:12][N:13]=2)[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C1(C2C=[CH:23][C:24](=[O:27])NN=2)C=CC=CC=1.[OH-].[K+].CO.BrCCO>CCCC[N+](CCCC)(CCCC)CCCC.[Br-].C1(C)C=CC=CC=1>[OH:27][CH2:24][CH2:23][N:12]1[C:11](=[O:14])[CH:10]=[CH:9][C:8]([C:2]2[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=2)=[N:13]1

Participants

8

Reactant 5

HCID 887MethanolHCID 108982-BromoethanolHCID 14797Potassium Hydroxide2×HCID 751063-Phenyl-6-pyridazoneHCID 701632586-Phenyl-3(2h)-pyridazinone potassium salt

Product 1

HCID 2121003(2H)-Pyridazinone, 2-(2-hydroxyethyl)-6-phenyl-Yield 87.9%

Reagents, catalysts & solvents 2

HCID 74236Tetrabutylammonium BromideCatalystHCID 1140TolueneSolvent

Procedure

A mixture of 6-phenyl-3(2H)-pyridazinone potassium salt (10 mmol) (prepared from 6-phenyl-3(2H)-pyridazinone (1.72 g; 10 mmol) and KOH in methanol (0.56 g; 10 mmol), 2-bromoethanol (12 mmol), TBAB (1.19 g; 4 mmol) and atomised KOH (11 mmol) in toluene (60 mL) was stirred at room temperature for 6 hours. The reaction mixture was filtered, the filtrate was washed successively with 5% NaOH solution, 10% HCl solution and lastly water. The organic extracts were dried over anhydrous Na2SO4 and concentrated to dryness, and the obtained residue was purified by flash chromatography (CH22Cl2MeOH 98:2), yielding the title product (1.9 g).

Workup

  1. filtrationThe reaction mixture was filtered
  2. washthe filtrate was washed successively with 5% NaOH solution, 10% HCl solution and lastly water
  3. dry with materialThe organic extracts were dried over anhydrous Na2SO4
  4. concentrationconcentrated to dryness
  5. customthe obtained residue was purified by flash chromatography (CH22Cl2MeOH 98:2)

Sources & evidence

ORD record
ord-52c168bfac7f4e6f9a773981f24fae1b
Source dataset
uspto-grants-2002_07
Patent number
US06413966B1

Reaction notes

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