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

HRID 367357Notes

Reaction equation

HRID 367357 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.

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-2451b33206af4f8e8e64568122ae9596
Source dataset
uspto-grants-2000_10
Patent number
US06133290

Reaction notes

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