4-Benzyloxy-1-methyl-5-pyridin-3-yl-1,3-dihydro-indol-2-one → 4-Hydroxy-1-methyl-5-pyridin-3-yl-1,3-dihydro-indol-2-one

HRID 1623556Notes

Reaction equation

HRID 1623556 reaction equation
C([O:8][C:9]1[C:17]([C:18]2[CH:19]=[N:20][CH:21]=[CH:22][CH:23]=2)=[CH:16][CH:15]=[C:14]2[C:10]=1[CH2:11][C:12](=[O:25])[N:13]2[CH3:24])C1C=CC=CC=1>C(O)C.[Pd]>[OH:8][C:9]1[C:17]([C:18]2[CH:19]=[N:20][CH:21]=[CH:22][CH:23]=2)=[CH:16][CH:15]=[C:14]2[C:10]=1[CH2:11][C:12](=[O:25])[N:13]2[CH3:24]

Participants

4

Reactant 1

HCID 667877154-Benzyloxy-1-methyl-5-pyridin-3-yl-1,3-dihydro-indol-2-one

Product 1

HCID 667938964-Hydroxy-1-methyl-5-pyridin-3-yl-1,3-dihydro-indol-2-one

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

To a solution of 4-benzyloxy-1-methyl-5-pyridin-3-yl-1,3-dihydro-indol-2-one (0.3 g, 0908 mmol) in ethanol (20 mL), was added 10% palladium on carbon (0.2 g, 0.28 mmol). The atmosphere over the reaction mixture was evacuated and the reaction was placed under an atmosphere of hydrogen gas via a balloon. The reaction was permitted to stir for 1 hour. The reaction mixture was then filtered through a plug of Celite®. The Celite pad was washed with hot ethanol (200 ml). The combined filtrate was then concentrated to afford 4-hydroxy-1-methyl-5-pyridin-3-yl-1,3-dihydro-indol-2-one; MS: (E 5÷) m/z 241.1 (M+H)+.

Workup

  1. customThe atmosphere over the reaction mixture was evacuated
  2. filtrationThe reaction mixture was then filtered through a plug of Celite®
  3. washThe Celite pad was washed with hot ethanol (200 ml)
  4. concentrationThe combined filtrate was then concentrated

Sources & evidence

ORD record
ord-72c136ade1e04a19a33afddc710372ab
Source dataset
uspto-grants-2014_07
Patent number
US08778972B2

Reaction notes

Loading…