[NH2:1][C:2]1[CH:3]=[C:4]([OH:9])[CH:5]=[CH:6][C:7]=1[CH3:8].[CH2:10](O)C>[Pd]>[OH:9][C:4]1[CH:3]=[C:2]2[C:7]([CH:8]=[CH:10][NH:1]2)=[CH:6][CH:5]=1The semicarbazone obtained above was reduced catalytically using 10% palladium on carbon in ethanol to yield a mixture of 6-hydroxyindole 38% yield, mp 124°-6° C., and 3-amino-4-methylphenol which were separated by column chromatography.
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