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Water → 9-Bromo-5-methyl-4-oxo-3-phenyl-3,5-dihydro-4H-pyridazino[4,5-b]indole-1-acetonitrile

HRID 1384820
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HRID 1384820 반응식
[Br:1][C:2]1[C:3]2[C:4]3[C:15]([CH2:16]Br)=[N:14][N:13]([C:18]4[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=4)[C:12](=[O:24])[C:5]=3[N:6]([CH3:11])[C:7]=2[CH:8]=[CH:9][CH:10]=1.[C-:25]#[N:26].[Na+].O>[Br-].C([N+](CCCC)(CCCC)CCCC)CCC.ClCCl>[Br:1][C:2]1[C:3]2[C:4]3[C:15]([CH2:16][C:25]#[N:26])=[N:14][N:13]([C:18]4[CH:19]=[CH:20][CH:21]=[CH:22][CH:23]=4)[C:12](=[O:24])[C:5]=3[N:6]([CH3:11])[C:7]=2[CH:8]=[CH:9][CH:10]=1
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

6

반응물 3

HCID 962WaterHCID 8929Sodium CyanideHCID 211837479-Bromo-1-(bromomethyl)-5-methyl-3-phenyl-3,5-dihydro-4H-pyridazino[4,5-b]indol-4-one

생성물 1

HCID 211837399-Bromo-5-methyl-4-oxo-3-phenyl-3,5-dihydro-4H-pyridazino[4,5-b]indole-1-acetonitrile수율 99.3%

시약·촉매·용매 2

HCID 74236Tetrabutylammonium Bromide촉매
HCID 6344Dichloromethane용매

실험 절차

A solution of 6.4 g (14.3 mmol) of 9-bromo-1-(bromomethyl)-5-methyl-3-phenyl-3,5-dihydro-4H-pyridazino[4,5-b]indol-4-one, of 3.6 g (73 mmol) of sodium cyanide and of 0.57 g (1 mmol) of tetrabutylammonium bromide in a mixture of 170 ml of dichloromethane and of 85 ml of water is heated at reflux for 3 h with mechanical stirring. Separation is carried out by settling and the reaction mixture is extracted with dichloromethane. The organic phase is washed with water and dried over sodium sulphate and the solvent is evaporated under reduced pressure. 5.6 g (14.2 mmol) of product are obtained, which product is used as is in the following stage.

후처리

  1. temperatureat reflux for 3 h with mechanical stirring
  2. customSeparation
  3. extractionthe reaction mixture is extracted with dichloromethane
  4. washThe organic phase is washed with water
  5. dry with materialdried over sodium sulphate
  6. customthe solvent is evaporated under reduced pressure

출처 및 근거

ORD 기록
ord-3883ee2d14b84014aee42e05a8dd198d
출처 데이터셋
uspto-grants-2001_07
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US06262045B1

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