[CH3:1][C:2]1[NH:3][C:4]2[C:9]([CH:10]=1)=[CH:8][C:7]([C:11]#N)=[CH:6][CH:5]=2.O.[PH2]([O-])=[O:15].[Na+].N1C=CC=CC=1>C(O)(=O)C.[Ni]>[CH3:1][C:2]1[NH:3][C:4]2[C:9]([CH:10]=1)=[CH:8][C:7]([CH:11]=[O:15])=[CH:6][CH:5]=2A 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.
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