Acetic Acid → 3-(5-Methyl-1H-indol-1-yl)propanenitrile

HRID 1756280Notes

Reaction equation

HRID 1756280 reaction equation
[CH3:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[NH:7][CH:6]=[CH:5]2.[OH-].C[N+:13](C)(C)[CH2:14][C:15]1C=CC=C[CH:16]=1.C(#N)C=C.C(O)(=O)C>O1CCOCC1>[CH3:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[N:7]([CH2:16][CH2:15][C:14]#[N:13])[CH:6]=[CH:5]2

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 7855AcrylonitrileHCID 119785-MethylindoleHCID 66854Benzyltrimethylammonium hydroxide

Product 1

HCID 156754313-(5-Methyl-1H-indol-1-yl)propanenitrile

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Conditions

Temperature
80 °C

Procedure

13 g (0.1 mol) of 5-methylindole are added to 4 ml of trimethylbenzylammonium hydroxide and 10 ml of acrylonitrile in 100 ml of dioxane while stirring. The mixture is then heated at 80° C. for 2 h and subsequently left to stand at room temperature for 3 days. Very dilute acetic acid is then added in order to neutralize the base. Extraction with EA (3×30 ml) is then carried out. The combined organic phases are dried with Na2SO4 and concentrated in vacuo. The residue was chromatographed on SiO2 with DIP as eluent. Rf [DIP]=0.3.

Workup

  1. waitsubsequently left
  2. extractionExtraction with EA (3×30 ml)
  3. dry with materialThe combined organic phases are dried with Na2SO4
  4. concentrationconcentrated in vacuo
  5. customThe residue was chromatographed on SiO2 with DIP as eluent

Sources & evidence

ORD record
ord-67eb468512984806986109704b6d5249
Source dataset
uspto-grants-1995_08
Patent number
US05440046

Reaction notes

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