[5-(3-diethylamino-propyl)-1H-indol-2-yl]-methanol → 5-(3-diethylamino-propyl)-1H-indole-2-carbaldehyde
Reaction equation
[CH2:1]([N:3]([CH2:18][CH3:19])[CH2:4][CH2:5][CH2:6][C:7]1[CH:8]=[C:9]2[C:13](=[CH:14][CH:15]=1)[NH:12][C:11]([CH2:16][OH:17])=[CH:10]2)[CH3:2]>ClCCl.[O-2].[Mn+2]>[CH2:18]([N:3]([CH2:1][CH3:2])[CH2:4][CH2:5][CH2:6][C:7]1[CH:8]=[C:9]2[C:13](=[CH:14][CH:15]=1)[NH:12][C:11]([CH:16]=[O:17])=[CH:10]2)[CH3:19]Participants
4
Reactant 1
Product 1
Reagents, catalysts & solvents 2
Procedure
Manganese oxide (3.75 g, 43.1 mmol) was added portionwise to [5-(3-diethylamino-propyl)-1H-indol-2-yl]-methanol (660 mg, 2.53 mmol) dissolved in dichloromethane (68 mL) under nitrogen at room temperature. The precipitate was filtered through celite, washing with hot dichloromethane. The filtrate was concentrated to give 563 mg (83%) of 5-(3-diethylamino-propyl)-1H-indole-2-carbaldehyde as a waxy brown solid.