Nitromethane → HCID 68553487, compound

HRID 2381275Notes

Reaction equation

HRID 2381275 reaction equation
[CH3:1][O:2][C:3]1[C:11](OC)=[CH:10][CH:9]=[C:8]2[C:4]=1[C:5]([CH:14]=O)=[CH:6][NH:7]2.[C:16]([O-:19])(=O)C.[NH4+].[N+:21]([CH3:24])([O-:23])=[O:22]>>[CH3:1][O:2][C:3]1[CH:11]=[CH:10][CH:9]=[C:8]2[C:4]=1[C:5]([CH:14]=[CH:24][N+:21]([O-:23])=[O:22])=[C:6]([O:19][CH3:16])[NH:7]2

Participants

4

Reactant 3

HCID 6375NitromethaneHCID 517165Ammonium AcetateHCID 111484124,5-dimethoxy-1H-indole-3-carbaldehyde

Product 1

HCID 68553487HCID 68553487, compoundYield 99%

Procedure

A solution of 4,5-dimethoxyindole-3-carbaldehyde (0.21 g, 1.02 mmol) and ammonium acetate (0.1268 g, 1.60 mmol) in nitromethane (10 cm3) was stirred at 70-75° C. under nitrogen for 11 hours using the method of Macor et al. The mixture was concentrated under vacuum and partitioned between water and ethyl acetate. The organic layer was washed with brine, dried with MgS04, and evaporated under vacuum to afford dimethoxy-3-(2-nitroethenyl)indole (0.25 g, 99%) as a brown solid.

Workup

  1. concentrationwas concentrated under vacuum
  2. custompartitioned between water and ethyl acetate
  3. washThe organic layer was washed with brine
  4. customdried with MgS04
  5. customevaporated under vacuum

Sources & evidence

ORD record
ord-7bb9da443a7a4a399cf5eeb0a64b80dd
Source dataset
uspto-grants-2012_09
Patent number
US08258173B2

Reaction notes

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