Nitromethane → (E)-4-chloro-3-(2-nitrovinyl)-1H-indole

HRID 2202699Notes

Reaction equation

HRID 2202699 reaction equation
[Cl:1][C:2]1[CH:10]=[CH:9][CH:8]=[C:7]2[C:3]=1[C:4]([CH:11]=O)=[CH:5][NH:6]2.C([O-])(=O)C.[NH4+].[N+:18]([CH3:21])([O-:20])=[O:19]>O>[Cl:1][C:2]1[CH:10]=[CH:9][CH:8]=[C:7]2[C:3]=1[C:4](/[CH:11]=[CH:21]/[N+:18]([O-:20])=[O:19])=[CH:5][NH:6]2

Participants

5

Reactant 3

HCID 6375NitromethaneHCID 517165Ammonium AcetateHCID 134990894-Chloro-1H-indole-3-carboxaldehyde

Product 1

HCID 21071472(E)-4-chloro-3-(2-nitrovinyl)-1H-indole

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
100 °C

Procedure

A mixture of 4-chloroindole-3-carbaldehyde (314 mg, 1.75 mmol) and ammonium acetate (404 mg, 5.25 mmol) in nitromethane (6 mL) was stirred at 100° C. for 20 min. The reaction mixture was cooled, diluted with water and extracted with EtOAc (2×40 mL). The combined organic layers were washed with brine, dried over MgSO4 and concentrated under reduced pressure. The crude material was purified by silicagel column chromatography (50-100% EtOAc/heptane) to give compound B19-1 (224 mg, 58%) as an orange solid.

Workup

  1. temperatureThe reaction mixture was cooled
  2. extractionextracted with EtOAc (2×40 mL)
  3. washThe combined organic layers were washed with brine
  4. dry with materialdried over MgSO4
  5. concentrationconcentrated under reduced pressure
  6. customThe crude material was purified by silicagel column chromatography (50-100% EtOAc/heptane)
  7. customto give compound B19-1 (224 mg, 58%) as an orange solid

Sources & evidence

ORD record
ord-667568d9aac94626bb7287d0d56df59a
Source dataset
uspto-grants-2016_06
Patent number
US09365522B2

Reaction notes

Loading…