2-[2-[2-(1,1-dimethyl-2-propenyl)-1H-indol-3-yl]ethyl]-1H-isoindole-1,3(2H)-dione → 2-(1,1-dimethyl-2-propenyl)-1H-indole-3-ethanamine
Reaction equation
[CH3:1][C:2]([C:6]1[NH:7][C:8]2[C:13]([C:14]=1[CH2:15][CH2:16][N:17]1C(=O)C3C(=CC=CC=3)C1=O)=[CH:12][CH:11]=[CH:10][CH:9]=2)([CH3:5])[CH:3]=[CH2:4]>CO.C(Cl)Cl>[CH3:5][C:2]([C:6]1[NH:7][C:8]2[C:13]([C:14]=1[CH2:15][CH2:16][NH2:17])=[CH:12][CH:11]=[CH:10][CH:9]=2)([CH3:1])[CH:3]=[CH2:4]Participants
3
Reactant 1
Product 1
Reagents, catalysts & solvents 1
Procedure
To a solution of 2-[2-[2-(1,1-dimethyl-2-propenyl)-1H-indol-3-yl]ethyl]-1H-isoindole-1,3(2H)-dione (1.10 g, 3.07 mmol) in 3:1 MeOH/CH2Cl2 (20 mL) at rt under argon was added N2H4H2O (0.52 mL). The reaction mixture was stirred overnight, concentrated in vacuo, diluted with CHCl3, then extracted with H2O. The CHCl3 layer was separated. The H2O layer was extracted further with CHCl3. The combined CHCl3 extracts were washed, dried, filtered, and concentrated to give the title compound: MS (ESI+) m/z 229.2.