5-Nitroindole → 3-(1,2,3,4,5,8-Hexahydroindolizin-7-yl)-5-nitro-1H-indole

HRID 277999Notes

Reaction equation

HRID 277999 reaction equation
[N+:1]([C:4]1[CH:5]=[C:6]2[C:10](=[CH:11][CH:12]=1)[NH:9][CH:8]=[CH:7]2)([O-:3])=[O:2].[CH2:13]1[CH:21]2[N:16]([CH2:17][CH2:18][C:19](=O)[CH2:20]2)[CH2:15][CH2:14]1>[OH-].[K+].O>[CH2:13]1[CH:21]2[N:16]([CH2:17][CH:18]=[C:19]([C:7]3[C:6]4[C:10](=[CH:11][CH:12]=[C:4]([N+:1]([O-:3])=[O:2])[CH:5]=4)[NH:9][CH:8]=3)[CH2:20]2)[CH2:15][CH2:14]1

Participants

5

Reactant 2

HCID 225235-NitroindoleHCID 11240524Octahydroindolizin-7-one

Product 1

HCID 153897603-(1,2,3,4,5,8-Hexahydroindolizin-7-yl)-5-nitro-1H-indoleYield 38.2%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 14797Potassium HydroxideSolvent

Procedure

A mixture of 5-nitro-1H-indole (4.48 g, 27.6 mmol) and and 7-octahydroindolizinone (5.0 g, 35.9 mmol) in methanolic potassium hydroxide (10% potassium hydroxide in 50 mL of methanol) was heated to reflux for 3.5 hours. The reaction was diluted with water and the precipitate was collected by filtration. The filter cake was triturated with hot diethyl ether and filtered. The filter cake was recrystallized from methanol and dried to give 2.99 g of the title compound. (38.5%). Calculated for C16H17N3O2: Theory: C, 67.83; H, 6.05; N, 14.83. Found: C, 68.07; H, 6.27; N, 14.82. MS(FD) (m/e): 283.

Workup

  1. temperaturewas heated
  2. temperatureto reflux for 3.5 hours
  3. filtrationthe precipitate was collected by filtration
  4. customThe filter cake was triturated with hot diethyl ether
  5. filtrationfiltered
  6. customThe filter cake was recrystallized from methanol
  7. customdried

Sources & evidence

ORD record
ord-54b9d806dc0e4dedab62672a7a350186
Source dataset
uspto-grants-2002_03
Patent number
US06358972B1

Reaction notes

Loading…