Water → 4-[3-Bromo-4-(4-bromo-but-2-enyloxy)-5-ethoxy-phenyl]-2-methyl-5-oxo-7-propyl-1,4,5,6,7,8-hexahydro-quinoline-3-carbonitrile

HRID 909378

반응식

HRID 909378 반응식
[Br:1][C:2]1[CH:3]=[C:4]([CH:12]2[C:21]3[C:20](=[O:22])[CH2:19][CH:18]([CH2:23][CH2:24][CH3:25])[CH2:17][C:16]=3[NH:15][C:14]([CH3:26])=[C:13]2[C:27]#[N:28])[CH:5]=[C:6]([O:9][CH2:10][CH3:11])[C:7]=1[OH:8].[Br:29][CH:30]=[CH:31][CH2:32][CH2:33]Br.C(=O)([O-])[O-].[K+].[K+].O>O1CCOCC1>[Br:1][C:2]1[CH:3]=[C:4]([CH:12]2[C:21]3[C:20](=[O:22])[CH2:19][CH:18]([CH2:23][CH2:24][CH3:25])[CH2:17][C:16]=3[NH:15][C:14]([CH3:26])=[C:13]2[C:27]#[N:28])[CH:5]=[C:6]([O:9][CH2:10][CH3:11])[C:7]=1[O:8][CH2:33][CH:32]=[CH:31][CH2:30][Br:29]

참가 물질

6

반응물 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 536293111,4-Dibromobut-1-eneHCID 670233814-(3-Bromo-5-ethoxy-4-hydroxy-phenyl)-2-methyl-5-oxo-7-propyl-1,4,5,6,7,8-hexahydro-quinoline-3-carbonitrile

생성물 1

HCID 674124544-[3-Bromo-4-(4-bromo-but-2-enyloxy)-5-ethoxy-phenyl]-2-methyl-5-oxo-7-propyl-1,4,5,6,7,8-hexahydro-quinoline-3-carbonitrile

시약·촉매·용매 1

HCID 312751,4-Dioxane용매

반응 조건

온도
80 °C

실험 절차

A mixture of 4-(3-bromo-5-ethoxy-4-hydroxy-phenyl)-2-methyl-5-oxo-7-propyl-1,4,5,6,7,8-hexahydro-quinoline-3-carbonitrile (3.04 g), 1,4-dibromobutene (11.68 g) and potassium carbonate (1.887 g) in dioxane (100 ml) was stirred at 80° C. for 5 h. The mixture was poured into water and extracted with dichloromethane. The organic layer was dried (MgSO4), filtered and concentrated in vacuo. The residue was dissolved in acetonitrile, washed with petroleum ether and heptane to remove most of the excess of dibromobutene. The acetonitrile layer was concentrated in vacuo and the residue recrystallized from dichloromethane and heptane. Yield: 3.02 g. MS-ESI: [M+H]+=579.2

후처리

  1. extractionextracted with dichloromethane
  2. dry with materialThe organic layer was dried (MgSO4)
  3. filtrationfiltered
  4. concentrationconcentrated in vacuo
  5. dissolutionThe residue was dissolved in acetonitrile
  6. washwashed with petroleum ether and heptane
  7. customto remove most of the excess of dibromobutene
  8. concentrationThe acetonitrile layer was concentrated in vacuo
  9. customthe residue recrystallized from dichloromethane and heptane

출처 및 근거

ORD 기록
ord-472e39a4e23e46c19639a19e3b86dc75
출처 데이터셋
uspto-grants-2011_09
특허 번호
US08017782B2

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