Pyridine → 2-methyl-1H-indole-5-carbaldehyde

Participants

Reaction Conditions

Reaction Steps

A mixture of 3.9 g 2-methyl-1H-indole-5-carbonitrile [Journal of Organic Chemistry (1994), 9(21), 6372-7], 7.22 g sodium hypophosphite monohydrate and 2.60 g Raney-Nickel in 110 ml acetic acid (50%)/pyridine 1:1 was stirred at 45° C. for 75 min. After cooling down to room temperature, the reaction mixture was filtered (dicalite), then the filtrate poured into ice-water and extracted 3 times with EtOAc. The combined organic phases were washed with water, dried over magnesium sulfate and evaporated. The residue was crystallized from n-heptane to give 3.19 g of 2-methyl-1H-indole-5-carbaldehyde as light red solid.

Provenance & Evidence