Piperidine → HCID 178437307, compound

HRID 2213687Notes

Reaction equation

HRID 2213687 reaction equation
[C:1]([C:4]1[N:5]=[CH:6][NH:7][CH:8]=1)(=O)[CH3:2].[N+:9]([C:12]1[CH:13]=[C:14]2[C:18](=[CH:19][CH:20]=1)[NH:17][C:16](=[O:21])[CH2:15]2)([O-:11])=[O:10].N1CCCCC1>>[N+:9]([C:12]1[CH:13]=[C:14]2[C:18](=[CH:19][CH:20]=1)[NH:17][C:16](=[O:21])[C:15]2=[C:1]([C:4]1[N:5]=[CH:6][NH:7][CH:8]=1)[CH3:2])([O-:11])=[O:10]

Participants

4

Reactant 3

HCID 8082PiperidineHCID 2303665-Nitro-2-oxindoleHCID 178467225HCID 178467225, compound

Product 1

HCID 178437307HCID 178437307, compoundYield 78.8%

Procedure

4-Acetylimidazole (0.7 g, 3.1 mmol) and 5-nitroindolin-2-one (0.56 g, 3.1 mmol) in sealed tube were heated in the presence of piperidine at 135° C. After 30 minutes, the reaction mixture was cooled to ambient temperature and concentrated. Recrystallization from ethanol afforded 0.66 g of 5-nitro-3-[1-(imidazol-4-yl)ethylidene]indolin-2-one.

Workup

  1. concentrationconcentrated
  2. customRecrystallization from ethanol

Sources & evidence

ORD record
ord-372a3aabe40b468f9f9e21d1e7bc91c9
Source dataset
uspto-grants-2006_09
Patent number
US07105563B2

Reaction notes

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