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

HRID 1029731Notes

Reaction equation

HRID 1029731 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

5

Reactant 2

HCID 190724043-Methyl-5-phenylmethoxy-1-(4-pyridinylamino)-1H-indoleHCID 178418361HCID 178418361, compound

Product 1

HCID 190723853-Methyl-1-(4-pyridinylamino)-1H-indol-5-ol

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

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.).

Workup

  1. customThe catalyst was removed by filtration through a pad of celite
  2. washthe solids washed with methanol
  3. concentrationConcentration and recrystallization from methanol
  4. customafforded 0.50 g of highly crystalline product, m.p. 239°-241° C. (dec.)

Sources & evidence

ORD record
ord-df32f13ebbe64f36a03cb457b196786d
Source dataset
uspto-grants-1992_04
Patent number
US05102891

Reaction notes

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