4-Nitrobenzaldehyde → 2-Methyl-3-(4-nitrobenzyl)-1H-indole

Participants

Reaction Steps

In an ice water bath, into a reaction vessel were added trifluoroacetic acid (6.824 g, 60 mmol), triethylsilane (13.9 g, 120 mmol), dichloromethane 20 mL. After stirring for 5 min, a dichloromethane solution dissolving 2-methyl-1H-indole (5.24 g, 40 mmol) and p-nitro benzaldehyde (6.67 g, 44 mmol) was added dropwise slowly into the reaction vessel. After completion of dropwise addition, it was reacted maintaining this temperature for 1 h. It was adjusted to pH=8-9 with 2 M solution of sodium hydroxide. An aqueous solution of sodium chloride was added, and extracted with dichloromethane. The extract was dried over anhydrous sodium sulfate, concentrated to dryness to obtain a red brown solid, and washed with diethyl ether to obtain a yellow powdered solid 4.3 g, at a yield of 40.3%.

Provenance & Evidence