4-Methyl-1h-indole-5-carbonitrile → 4-methyl-1H-indole-5-carbaldehyde

HRID 2181197Notes

Reaction equation

HRID 2181197 reaction equation
[CH3:1][C:2]1[C:10]([C:11]#N)=[CH:9][CH:8]=[C:7]2[C:3]=1[CH:4]=[CH:5][NH:6]2.O.[PH2]([O-])=[O:15].[Na+]>C(O)(=O)C.N1C=CC=CC=1.[Ni]>[CH3:1][C:2]1[C:10]([CH:11]=[O:15])=[CH:9][CH:8]=[C:7]2[C:3]=1[CH:4]=[CH:5][NH:6]2

Participants

5

Reactant 2

HCID 224856884-Methyl-1h-indole-5-carbonitrileHCID 178418950HCID 178418950, compound

Product 1

HCID 224856734-methyl-1H-indole-5-carbaldehyde

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 165292Pyridinium acetateSolvent

Procedure

In analogy to the procedure described in preparation 5a), 4-methyl-1H-indole-5-carbonitrile was reacted with sodium hypophosphite monohydrate and Raney-Nickel in acetic acid/pyridine to give 4-methyl-1H-indole-5-carbaldehyde as light yellow solid.

Sources & evidence

ORD record
ord-6e47b176a5404948a4448f940052439f
Source dataset
uspto-grants-2005_05
Patent number
US06890947B2

Reaction notes

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