N-{3-[4-(5-Benzyloxypyridin-2-yloxy)phenyl]-1-methylpropyl}acetamide → N-{3-[4-(5-Hydroxypyridin-2-yloxy)phenyl]-1-methylpropyl}acetamide

HRID 1260513Notes

Reaction equation

HRID 1260513 reaction equation
C([O:8][C:9]1[CH:10]=[CH:11][C:12]([O:15][C:16]2[CH:21]=[CH:20][C:19]([CH2:22][CH2:23][CH:24]([NH:26][C:27](=[O:29])[CH3:28])[CH3:25])=[CH:18][CH:17]=2)=[N:13][CH:14]=1)C1C=CC=CC=1.[H][H]>C(O)C.[Pd]>[OH:8][C:9]1[CH:10]=[CH:11][C:12]([O:15][C:16]2[CH:21]=[CH:20][C:19]([CH2:22][CH2:23][CH:24]([NH:26][C:27](=[O:29])[CH3:28])[CH3:25])=[CH:18][CH:17]=2)=[N:13][CH:14]=1

Participants

5

Reactant 2

HCID 44608622N-{3-[4-(5-Benzyloxypyridin-2-yloxy)phenyl]-1-methylpropyl}acetamideHCID 178418361HCID 178418361, compound

Product 1

HCID 67302795N-{3-[4-(5-Hydroxypyridin-2-yloxy)phenyl]-1-methylpropyl}acetamide

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

N-{3-[4-(5-Benzyloxypyridin-2-yloxy)phenyl]-1-methylpropyl}acetamide (344 mg, 881 μmol) were dissolved in 20 ml of ethanol. Addition of 93 mg of palladium/carbon was followed by hydrogenation under a pressure of 5 bar of hydrogen at room temperature for 16 h. The catalyst was filtered off and the filtrate was concentrated. Yield: 220 mg (83%), M+H+: 301.13.

Workup

  1. filtrationThe catalyst was filtered off
  2. concentrationthe filtrate was concentrated

Sources & evidence

ORD record
ord-a2112695a10d44f2bdbf698426baa665
Source dataset
uspto-grants-2013_06
Patent number
US08470841B2

Reaction notes

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