Acrylonitrile → Benzyl 1-(2-cyanoethyl)-2-indolecarboxylate

HRID 844434Notes

Reaction equation

HRID 844434 reaction equation
[C:1](#[N:4])[CH:2]=[CH2:3].[NH:5]1[C:13]2[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=2)[CH:7]=[C:6]1[C:14]([O:16][CH2:17][C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1)=[O:15]>O.O1CCOCC1>[C:1]([CH2:2][CH2:3][N:5]1[C:13]2[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=2)[CH:7]=[C:6]1[C:14]([O:16][CH2:17][C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1)=[O:15])#[N:4]

Participants

5

Reactant 2

HCID 7855AcrylonitrileHCID 7723355benzyl 1H-indole-2-carboxylate

Product 1

HCID 22612661Benzyl 1-(2-cyanoethyl)-2-indolecarboxylate

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 312751,4-DioxaneSolvent

Conditions

Temperature
80 °C

Procedure

1.6 ml of Triton B at 40% in water and 4 ml of acrylonitrile are mixed in 40 ml of dioxane, and 9.44 g of benzyl 2-indolecarboxylate are then added with stirring. The mixture is heated at 80° C. for 24 hours and is then poured into 500 ml of ice-cold water. The precipitate formed is filtered off, taken up in EtOAc and this solution is then dried over Na2SO4 and concentrated to give 10.1 g of the expected compound, which crystallizes: m.p.=98-100° C.

Workup

  1. customThe precipitate formed
  2. filtrationis filtered off
  3. dry with materialthis solution is then dried over Na2SO4
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-6c19af5a662c4cf3b5cb8f5c63da6264
Source dataset
uspto-grants-2002_04
Patent number
US06380230B1

Reaction notes

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