Nitromethane → 5-Benzyl-3-(2-nitroethenyl)indole

HRID 1720066Notes

Reaction equation

HRID 1720066 reaction equation
[CH2:1]([C:8]1[CH:9]=[C:10]2[C:14](=[CH:15][CH:16]=1)[NH:13][CH:12]=[C:11]2[CH:17]=O)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C([O-])(=O)C.[NH4+].[N+:24]([CH3:27])([O-:26])=[O:25]>>[CH2:1]([C:8]1[CH:9]=[C:10]2[C:14](=[CH:15][CH:16]=1)[NH:13][CH:12]=[C:11]2[CH:17]=[CH:27][N+:24]([O-:26])=[O:25])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

4

Reactant 3

HCID 6375NitromethaneHCID 517165Ammonium AcetateHCID 224199495-Benzyl-3-formylindole

Product 1

HCID 544807005-Benzyl-3-(2-nitroethenyl)indoleYield 34%

Procedure

The aidehyde 5-benzyl-3-formylindole (0.15 g, 0.6 mmol), nitromethane (0.9 ml) and ammonium acetate (0.05 g, 0.7 mmol) were heated gently under reflux for 0.5 h. On cooling, dark ruby-red crystals slowly separated. Crystallization from methanol gave 0.06 g (34%) of 5-benzyl-3-(2-nitroethenyl)indole as orange crystals.

Workup

  1. temperatureunder reflux for 0.5 h
  2. temperatureOn cooling
  3. customdark ruby-red crystals slowly separated
  4. customCrystallization from methanol

Sources & evidence

ORD record
ord-2d33d545fdde434f935645275ad74aa6
Source dataset
uspto-grants-1996_04
Patent number
US05504101

Reaction notes

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