Nitromethane → 5-(2-nitro-vinyl)-1H-indole

HRID 128971Notes

Reaction equation

HRID 128971 reaction equation
[NH:1]1[C:9]2[C:4](=[CH:5][C:6]([CH:10]=O)=[CH:7][CH:8]=2)[CH:3]=[CH:2]1.C([O-])(=O)C.[NH4+].[N+:17]([CH3:20])([O-:19])=[O:18]>>[N+:17]([CH:20]=[CH:10][C:6]1[CH:5]=[C:4]2[C:9](=[CH:8][CH:7]=1)[NH:1][CH:2]=[CH:3]2)([O-:19])=[O:18]

Participants

4

Reactant 3

HCID 6375NitromethaneHCID 517165Ammonium AcetateHCID 589040Indole-5-carboxaldehyde

Product 1

HCID 544650165-(2-nitro-vinyl)-1H-indole

Conditions

Temperature
110 °C

Procedure

A mixture of the product from step (a) (7.5 g), ammonium acetate (1.5 g) and nitromethane (77 ml) was heated at 110° C. for 2 hours, then cooled and evaporated in vacuo. The residue was triturated with water to give the desired product as a yellow solid which was filtered off and dried (9.2 g).

Workup

  1. temperaturecooled
  2. customevaporated in vacuo
  3. customThe residue was triturated with water

Sources & evidence

ORD record
ord-991371198bfa4078bd4f3707a9424f5e
Source dataset
uspto-grants-1995_11
Patent number
US05466699

Reaction notes

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