Nitromethane → 2-Nitrovinyl-5-cyano-1H-indole

HRID 1371855

Reaction equation

HRID 1371855 reaction equation
C([C:3]1[C:11]2[C:6](=[CH:7][CH:8]=[C:9]([C:12]#[N:13])[CH:10]=2)[NH:5][CH:4]=1)=O.[C:14]([O-])(=O)[CH3:15].[NH4+].[N+:19](C)([O-:21])=[O:20]>>[N+:19]([CH:14]=[CH:15][N:5]1[C:6]2[C:11](=[CH:10][C:9]([C:12]#[N:13])=[CH:8][CH:7]=2)[CH:3]=[CH:4]1)([O-:21])=[O:20]

Participants

4

Reactant 3

HCID 6375NitromethaneHCID 285043-Formyl-1H-indole-5-carbonitrileHCID 517165Ammonium Acetate

Product 1

HCID 698506202-Nitrovinyl-5-cyano-1H-indole

Conditions

Temperature
90 °C

Procedure

Combine 3-formyl-5-cyano-1H-indole (10.60 g, 63.32 mmol) and a solution of ammonium acetate (10.60 g) in nitromethane (660 ml). Heat to 90° C. After 2 hours, cool to ambient temperature to give a precipitate. Collect the precipitate by filtration, wash with 1:1 MeOH/water (500 ml), and dry to give the title compound: mp 247–251° C. MS (ACPI): m/e 214.0 (M+1).

Workup

  1. temperaturecool to ambient temperature
  2. customto give a precipitate
  3. customCollect the precipitate
  4. filtrationby filtration
  5. washwash with 1:1 MeOH/water (500 ml)
  6. customdry

Sources & evidence

ORD record
ord-6ff82343e32349d3b0127c8cde43532f
Source dataset
uspto-grants-2007_01
Patent number
US07157488B2

Linked notes

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