3-Methyl-5-phenylmethoxy-1-(4-pyridinylamino)-1H-indole → 3-Methyl-1-(4-pyridinylamino)-1H-indol-5-ol

Reaction equation

[CH3:1][C:2]1[C:10]2[C:5](=[CH:6][CH:7]=[C:8]([O:11]CC3C=CC=CC=3)[CH:9]=2)[N:4]([NH:19][C:20]2[CH:25]=[CH:24][N:23]=[CH:22][CH:21]=2)[CH:3]=1.[H][H]>C(O)C.[Pd]>[CH3:1][C:2]1[C:10]2[C:5](=[CH:6][CH:7]=[C:8]([OH:11])[CH:9]=2)[N:4]([NH:19][C:20]2[CH:25]=[CH:24][N:23]=[CH:22][CH:21]=2)[CH:3]=1

Participants

Procedure

3-Methyl-5-phenylmethoxy-1-(4-pyridinylamino)-1H-indole (2.20 g) was subjected to hydrogenolysis in absolute ethanol (80 ml) with 10% Pd-C (0.26 g) at 50 psig hydrogen at 50° C. for 2 hours. The catalyst was removed by filtration through a pad of celite and the solids washed with methanol. Concentration and recrystallization from methanol afforded 0.50 g of highly crystalline product, m.p. 239°-241° C. (dec.).