5-对硝基苯基糠醛 → 3-(3-((5-(4-Nitrophenyl)furan-2-yl)methylene)-3,4,5,6-tetrahydropyridin-2-yl)pyridine

HRID 1678323

反应方程式

HRID 1678323 反应方程式
[Cl-].[NH3+:2][CH2:3][CH2:4][CH2:5][CH2:6][C:7]([C:9]1[CH:10]=[NH+:11][CH:12]=[CH:13][CH:14]=1)=O.[Cl-].[N+:16]([C:19]1[CH:24]=[CH:23][C:22]([C:25]2[O:31][C:28]([CH:29]=O)=[CH:27][CH:26]=2)=[CH:21][CH:20]=1)([O-:18])=[O:17]>C(O)(C)C>[N+:16]([C:19]1[CH:20]=[CH:21][C:22]([C:25]2[O:31][C:28]([CH:29]=[C:6]3[CH2:5][CH2:4][CH2:3][N:2]=[C:7]3[C:9]3[CH:10]=[N:11][CH:12]=[CH:13][CH:14]=3)=[CH:27][CH:26]=2)=[CH:23][CH:24]=1)([O-:18])=[O:17]

参与物

4

反应物 2

HCID 815675-对硝基苯基糠醛HCID 673376573-(5-Ammoniopentanoyl)pyridinium chloride

产物 1

HCID 673391433-(3-((5-(4-Nitrophenyl)furan-2-yl)methylene)-3,4,5,6-tetrahydropyridin-2-yl)pyridine收率 36.6%

试剂、催化剂与溶剂 1

HCID 3776异丙醇溶剂

反应条件

温度
80 °C

实验过程

3-(5-Ammoniopentanoyl)pyridinium chloride (95 mg, 0.38 mmol) and 5-(4-nitrophenyl)furfural (99 mg, 0.46 mmol) were combined in a reaction vessel and treated with isopropanol (6 mL). The reaction vessel was sealed and the reaction was heated to 80° C. with stirring overnight. The reaction was then cooled to room temperature, concentrated under reduced pressure and treated with saturated NaHCO3(aq). This mixture was then extracted three times with EtOAc. The EtOAc extracts were washed with brine, combined, dried over Na2SO4, filtered and concentrated under reduced pressure. The recovered material was eluted through a 20 gram column of silica gel with 10.5:7:7:1:0.1 hexane:MtBE:CH2Cl2:MeOH:NH4OH (1 liter). One sample was recovered that appeared to be highly crystalline. This material was re-crystallized from hot methanol. The crystals were recovered by vacuum filtration, washed with isopropanol then dried under vacuum giving 50 mg (36%) of an orange crystalline solid. LC-MS: RT=5.16 min, [M+H]+=360.0.

后处理

  1. customThe reaction vessel was sealed
  2. temperatureThe reaction was then cooled to room temperature
  3. concentrationconcentrated under reduced pressure
  4. additiontreated with saturated NaHCO3(aq)
  5. extractionThis mixture was then extracted three times with EtOAc
  6. washThe EtOAc extracts were washed with brine
  7. dry with materialdried over Na2SO4
  8. filtrationfiltered
  9. concentrationconcentrated under reduced pressure
  10. washThe recovered material was eluted through a 20 gram column of silica gel with 10.5:7:7:1:0.1 hexane
  11. customOne sample was recovered
  12. customThis material was re-crystallized from hot methanol
  13. filtrationThe crystals were recovered by vacuum filtration
  14. washwashed with isopropanol
  15. customthen dried under vacuum

来源与证据

ORD记录
ord-c61eacb8a004462aac695b8c1fa180f0
来源数据集
uspto-grants-2011_08
专利号
US08008499B2

关联笔记

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