Acrylonitrile → HCID 18976205, compound

Reaction equation

[Cl:1][C:2]1[CH:3]=[C:4]([CH:23]=[CH:24][C:25]=1[Cl:26])[C:5]([NH:7][CH:8]1[C:16]2[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=2)[N:10]([CH2:17][CH2:18][CH2:19][CH2:20][CH3:21])[C:9]1=[O:22])=[O:6].[C:27](#[N:30])[CH:28]=[CH2:29].C(=O)([O-])[O-].[K+].[K+]>CC(C)=O>[Cl:1][C:2]1[CH:3]=[C:4]([CH:23]=[CH:24][C:25]=1[Cl:26])[C:5]([NH:7][C:8]1([CH2:29][CH2:28][C:27]#[N:30])[C:16]2[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=2)[N:10]([CH2:17][CH2:18][CH2:19][CH2:20][CH3:21])[C:9]1=[O:22])=[O:6]

Participants

Procedure

Under argon atmosphere, a mixture of 2.70 g of 3,4-dichloro-N-(2,3-dihydro-2-oxo-1-pentyl-1H-indol-3-yl)benzamide, 1.30 g of acrylonitrile, 30 ml of acetone and 1.46 g of potassium carbonate was stirred at room temperature for 1 hour. After removal of solvent, the residue was treated with water and extracted with ethyl acetate. After the ethyl acetate extract was washed and dried, the solvent was removed by evaporation. The residue was crystallized from ethyl acetate-hexane to afford 2.28 g of 3,4-dichloro-N-[3-(2-cyanoethyl)-2,3-dihydro-2-oxo-1-pentyl-1H-indol-3-yl]-benzamide as colorless crystals. Melting point: 79° to 84° C., IR (Nujol) (cm-1): 3340, 2325, 1700, 1655, 1610, MS (m/z): 445 & 443 (M+).