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

HRID 363318Notes

Reaction equation

HRID 363318 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>>[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

3

Reactant 2

HCID 225235-NitroindoleHCID 11240524Octahydroindolizin-7-one

Product 1

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

Procedure

The 5-nitro-1H-indole (4.48 g, 27.6 mmol) and 7-octahydroindolizinone (5.0 g, 35.9 mmol) were converted to product by the procedure of Preparation IV to yield 2.99 g. (38.5%).

Workup

  1. customto yield 2.99 g

Sources & evidence

ORD record
ord-dc789c06cbeb4af192eb5bdbdb983a48
Source dataset
uspto-grants-1999_02
Patent number
US05874427

Reaction notes

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