4-benzyloxy-1-(3-fluorobenzyl)-1H-pyridin-2-one → HCID 54724162, compound

HRID 1866919Notes

Reaction equation

HRID 1866919 reaction equation
C([O:8][C:9]1[CH:14]=[CH:13][N:12]([CH2:15][C:16]2[CH:21]=[CH:20][CH:19]=[C:18]([F:22])[CH:17]=2)[C:11](=[O:23])[CH:10]=1)C1C=CC=CC=1>CCO.[Pd]>[F:22][C:18]1[CH:17]=[C:16]([CH:21]=[CH:20][CH:19]=1)[CH2:15][N:12]1[CH:13]=[CH:14][C:9]([OH:8])=[CH:10][C:11]1=[O:23]

Participants

4

Reactant 1

HCID 220502224-benzyloxy-1-(3-fluorobenzyl)-1H-pyridin-2-one

Product 1

HCID 54724162HCID 54724162, compoundYield 72.4%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

To a solution of 4-benzyloxy-1-(3-fluorobenzyl)-1H-pyridin-2-one (1.79 g, 5.8 mmol) in EtOH (50 mL) was added 10% Pd/C (0.4 g), and reaction mixture was stirred under a hydrogen atmosphere for 1.5 h. The reaction mixture was filtered through diatomaceous earth and concentrated under reduced pressure to give 1-(3-fluorobenzyl)-4-hydroxy-1H-pyridin-2-one (0.92 g, 72%): 1H NMR (300 MHz, CDCl3) δ 7.55 (d, J=6 Hz, 1H), 7.40-7.30 (m, 1H), 7.10-6.95 (m, 3H), 6.07 (dd, J=6, 3 Hz, 1H), 5.85 (d, J=3 Hz, 1H), 5.11 (s, 2H).

Workup

  1. filtrationThe reaction mixture was filtered through diatomaceous earth
  2. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-5bcd84323aa843ba802468b67572d3f8
Source dataset
uspto-grants-2009_12
Patent number
US07629363B2

Reaction notes

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