Methyl iodide → 2-(2-Methoxyethyl)-4-phenyl-1(2H)-phthalazinone

HRID 1769120Notes

Reaction equation

HRID 1769120 reaction equation
[C:1]([C:9]1[CH:17]=[CH:16][CH:15]=[CH:14][C:10]=1[C:11]([OH:13])=O)(=O)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[OH:18][CH2:19][CH2:20][NH:21][NH2:22].O[CH2:24]CC1C2C(=CC=CC=2)C(=O)NN=1.[H-].[Na+].[H][H].CI>CN(C=O)C.O.C1COCC1>[CH3:24][O:18][CH2:19][CH2:20][N:21]1[N:22]=[C:1]([C:2]2[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=2)[C:9]2[C:10](=[CH:14][CH:15]=[CH:16][CH:17]=2)[C:11]1=[O:13]

Participants

10

Reactant 6

HCID 6328Methyl iodideHCID 68132-Benzoylbenzoic AcidHCID 80172-HydrazinoethanolHCID 24758Sodium hydrideHCID 14322325Hydroxyethyl-phthalazinoneHCID 178418361HCID 178418361, compound

Product 1

HCID 199570712-(2-Methoxyethyl)-4-phenyl-1(2H)-phthalazinoneYield 47%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6228DimethylformamideSolventHCID 8028TetrahydrofuranSolvent

Procedure

Eighty-five grams (0.38 mole) of 2-benzoylbenzoic acid and 28.6 g (0.38 mole) of hydroxyethylhydrazine were reacted according to the procedure of Example 185. The resulting hydroxyethyl-phthalazinone was suspended in 300 mL of DMF and 200 mL THF and 12.3 g of 60% sodium hydride in oil was added in portions over 40 minutes under nitrogen. The reaction was stirred an additional 45 minutes at room temperature and the evolution of hydrogen ceased. Thirty-one milliliters of methyl iodide was added over 1.5 hours and the reaction was stirred at gentle reflux for 16 hours. It was poured into water and extracted into ether. The ether layers were dried over sodium sulfate and stripped. The residue was chromatographed on silica with 5% ethylamine in ethyl acetate to provide 39 g (47%) of product, mp 115-118 after recrystallization from cyclohexane.

Workup

  1. stirringthe reaction was stirred
  2. temperatureat gentle reflux for 16 hours
  3. extractionextracted into ether
  4. dry with materialThe ether layers were dried over sodium sulfate
  5. customThe residue was chromatographed on silica with 5% ethylamine in ethyl acetate

Sources & evidence

ORD record
ord-1c41622f971849be8f558a064cf61833
Source dataset
uspto-grants-1995_01
Patent number
US05380721

Reaction notes

Loading…