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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
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HRID 915003 반응식
[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]
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참가 물질

6

반응물 3

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

생성물 1

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

시약·촉매·용매 2

HCID 8028Tetrahydrofuran용매HCID 8857
Ethyl Acetate
용매

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온도
47.5 °C

실험 절차

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).

후처리

  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)

출처 및 근거

ORD 기록
ord-2fd5f3883747406db7332d242ba5605c
출처 데이터셋
uspto-grants-2007_09
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US07265120B2

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