N-Methyl-5-benzyloxyindole → 1-Methyl-1H-indol-5-ol

HRID 603392Notes

Reaction equation

HRID 603392 reaction equation
C([O:8][C:9]1[CH:10]=[C:11]2[C:15](=[CH:16][CH:17]=1)[N:14]([CH3:18])[CH:13]=[CH:12]2)C1C=CC=CC=1.C([O-])=O.[NH4+]>CCO.[OH-].[Pd+2].[OH-]>[CH3:18][N:14]1[C:15]2[C:11](=[CH:10][C:9]([OH:8])=[CH:17][CH:16]=2)[CH:12]=[CH:13]1

Participants

5

Reactant 2

HCID 259196N-Methyl-5-benzyloxyindoleHCID 2723923Ammonium formate

Product 1

HCID 108445251-Methyl-1H-indol-5-olYield 90%

Reagents, catalysts & solvents 2

HCID 9942167Palladium hydroxideCatalystHCID 702EthanolSolvent

Conditions

Temperature
35 °C

Procedure

5-(Benzyloxy)-1-methyl-1H-indole (Example 46, 254 mg, 1.07 mmol) was dissolved in EtOH (15 mL) and 20% palladium (II) hydroxide on carbon (30.0 mg) was added. Ammonium formate (540 mg, 8.6 mmol) was added, and the mixture was stirred for 30 min at rt and subsequently for 2 h at 35° C. The catalyst was removed by filtration, and the filtrate was concentrated under reduced pressure. The residue was taken up in water, and the aqueous solution was extracted with EtOAc (2×). The combined organic phases were dried over Na2SO4, filtered, and concentrated under reduced pressure to provide 141 mg (90%) of the title compound as a white crystalline solid. 1H NMR (400 MHz, CDCl3): δ 3.78 (s, 3H), 6.33 (br, 1H), 6.79 (d, 1H), 7.03 (br, 2H), 7.19 (d, 1H).

Workup

  1. customThe catalyst was removed by filtration
  2. concentrationthe filtrate was concentrated under reduced pressure
  3. extractionthe aqueous solution was extracted with EtOAc (2×)
  4. dry with materialThe combined organic phases were dried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-eb2ce5d8a8534e66b9dab08efd047d51
Source dataset
uspto-grants-2011_03
Patent number
US07906653B2

Reaction notes

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