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Isoamyl Nitrite → 1-(1-Isopropyl-6-oxo-1,6-dihydro-3-pyridazinyl)-2-phenyl-1,2-ethanedione 1-oxime

HRID 915003
ノート
印刷プレビュー

反応式

HRID 915003 の反応式
[CH:1]([N:4]1[C:9](=[O:10])[CH:8]=[CH:7][C:6]([CH2:11][C:12](=[O:19])[C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)=[N:5]1)([CH3:3])[CH3:2].[H-].[Na+].[N:22](OCCC(C)C)=[O:23]>C1COCC1.CCOC(C)=O>[CH:1]([N:4]1[C:9](=[O:10])[CH:8]=[CH:7][C:6]([C:11](=[N:22][OH:23])[C:12]([C:13]2[CH:14]=[CH:15][CH:16]=[CH:17][CH:18]=2)=[O:19])=[N:5]1)([CH3:3])[CH3:2]
参加物反応条件実験手順後処理出典と根拠反応ノート

参加物

6

反応物 3

HCID 8053Isoamyl NitriteHCID 24758Sodium hydrideHCID 693314642-isopropyl-6-(2-oxo-2-phenylethyl)-3(2H)-pyridazinone

生成物 1

HCID 1363499311-(1-Isopropyl-6-oxo-1,6-dihydro-3-pyridazinyl)-2-phenyl-1,2-ethanedione 1-oxime

試薬・触媒・溶媒 2

HCID 8028Tetrahydrofuran溶媒HCID 8857
Ethyl Acetate
溶媒

反応条件

温度
47.5 °C

実験手順

Under nitrogen atmosphere, 2-isopropyl-6-(2-oxo-2-phenylethyl)-3(2H)-pyridazinone (513 mg) was added to a suspension of NaH (60% dispersion in mineral oil) (84 mg) in THF (5 ml) and the mixture was stirred at 45-50° C. for 30 minutes. After addition of isoamyl nitrite (0.27 ml), the mixture was stirred at the same temperature for 8 hours. The mixture was dissolved in EtOAc, washed with 1N HCl and brine and dried over MgSO4. The mixture was concentrated under reduced pressure and subjected to column chromatography on silica gel eluting with a mixture of n-hexane and EtOAc (50:50 v/v) to give 1-(1-isopropyl-6-oxo-1,6-dihydro-3-pyridazinyl)-2-phenyl-1,2-ethanedione 1-oxime as a solid (185 mg).

後処理

  1. stirringthe mixture was stirred at the same temperature for 8 hours
  2. washwashed with 1N HCl and brine
  3. dry with materialdried over MgSO4
  4. concentrationThe mixture was concentrated under reduced pressure
  5. additionsubjected to column chromatography on silica gel eluting with a mixture of n-hexane and EtOAc (50:50 v/v)

出典と根拠

ORDレコード
ord-2fd5f3883747406db7332d242ba5605c
出典データセット
uspto-grants-2007_09
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US07265120B2

反応ノート

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