Water → HCID 22417719, compound

Participants

Reaction Steps

A mixture of 16 g (0.06 mol) of 2-(2-chlorobenzyl)-6-nitrotoluene and 24.4 g (0.09 mol) of tripiperidinomethane is heated for 5 hours at 120° C. in a water jet vacuum with interconnection of a distillation assembly. Then the mixture is taken up in 200 ml of a mixture of 5 parts of toluene and 3 parts of glacial acetic acid and under stirring is added to a suspension of 144 g of iron powder and 362 g of silica gel in 800 ml the same toluene-glacial acetic acid mixture. The reaction mixture is refluxed for 1 hour under an argon atmosphere. After cooling it is diluted with methylene chloride and filtered off from a precipitate. The filtrate in succession is washed with 10% sodium carbonate solution, 5% sodium bisulfite solution and saturated common salt solution and then dried on sodium sulfate. The solution is concentrated by evaporation, the residue after chromatography on silica gel with a mixture of 4 parts of cyclohexane and one part of ethyl acetate and recrystallization from cyclohexane yields 9 g (58% of theory) of 4-(2-chlorobenzyl)-indole, melting point 76°-77° C.

Provenance & Evidence