4-(benzyloxy)-1-(4-(2-hydroxy-2-methylpropoxy)-3-methoxyphenyl)pyridin-2(1H)-one → 4-hydroxy-1-(4-(2-hydroxy-2-methylpropoxy)-3-methoxyphenyl)pyridin-2(1H)-one

HRID 1044403Notes

Reaction equation

HRID 1044403 reaction equation
C([O:8][C:9]1[CH:14]=[CH:13][N:12]([C:15]2[CH:20]=[CH:19][C:18]([O:21][CH2:22][C:23]([OH:26])([CH3:25])[CH3:24])=[C:17]([O:27][CH3:28])[CH:16]=2)[C:11](=[O:29])[CH:10]=1)C1C=CC=CC=1>CO.[Pd]>[OH:8][C:9]1[CH:14]=[CH:13][N:12]([C:15]2[CH:20]=[CH:19][C:18]([O:21][CH2:22][C:23]([OH:26])([CH3:24])[CH3:25])=[C:17]([O:27][CH3:28])[CH:16]=2)[C:11](=[O:29])[CH:10]=1

Participants

4

Reactant 1

HCID 585802644-(benzyloxy)-1-(4-(2-hydroxy-2-methylpropoxy)-3-methoxyphenyl)pyridin-2(1H)-one

Product 1

HCID 585802934-hydroxy-1-(4-(2-hydroxy-2-methylpropoxy)-3-methoxyphenyl)pyridin-2(1H)-oneYield 98%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

A mixture of 4-(benzyloxy)-1-(4-(2-hydroxy-2-methylpropoxy)-3-methoxyphenyl)pyridin-2(1H)-one Part B (287 mg, 0.73 mmol) and 10% Pd/C (7.72 mg, 0.073 mmol) in MeOH (15 mL) was hydrogenated at 50 PSI of H2 for 4 hours. Pd/C was filtered off and the filtrate was concentrated giving 4-hydroxy-1-(4-(2-hydroxy-2-methylpropoxy)-3-methoxyphenyl)pyridin-2(1H)-one 7C (228 mg, 98% yield).

Workup

  1. filtrationPd/C was filtered off
  2. concentrationthe filtrate was concentrated

Sources & evidence

ORD record
ord-7c1a325aab9b4796a11d545cc0f8728a
Source dataset
uspto-grants-2013_10
Patent number
US08563583B2

Reaction notes

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