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

HRID 54975

Reaktionsgleichung

Reaktionsgleichung von HRID 54975
[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]

Komponenten

10

Edukt 6

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

Produkt 1

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

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 962WaterLösungsmittelHCID 6228DimethylformamideLösungsmittelHCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

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.

Aufarbeitung

  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

Quellen und Nachweise

ORD-Eintrag
ord-21297e0e110f42bc94fefd9751f49c00
Quelldatensatz
uspto-grants-1997_04
Patentnummer
US05624922

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