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

HRID 54975

反応式

HRID 54975 の反応式
[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]

参加物

10

反応物 6

HCID 6328Methyl iodideHCID 68132-Benzoylbenzoic AcidHCID 80172-HydrazinoethanolHCID 24758Sodium hydrideHCID 14322325Hydroxyethyl-phthalazinoneHCID 178418361HCID 178418361、化合物

生成物 1

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

試薬・触媒・溶媒 3

HCID 962Water溶媒HCID 6228Dimethylformamide溶媒HCID 8028Tetrahydrofuran溶媒

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-21297e0e110f42bc94fefd9751f49c00
出典データセット
uspto-grants-1997_04
特許番号
US05624922

関連ノート

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