Methanol → HCID 18366518, compound

HRID 379519Notes

Reaction equation

HRID 379519 reaction equation
[CH2:1]([N:8]1[CH:13]=[CH:12][C:11](=[O:14])[CH2:10][CH:9]1C1C=CC=CC=1OC)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4]C=1.[CH3:23][OH:24]>[OH-].[OH-].[Pd+2]>[CH3:23][O:24][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:1]=1[N:8]1[CH2:9][CH2:10][CH:11]([OH:14])[CH2:12][CH2:13]1

Participants

4

Reactant 2

HCID 887MethanolHCID 15884730HCID 15884730, compound

Product 1

HCID 18366518HCID 18366518, compound

Reagents, catalysts & solvents 1

HCID 9942167Palladium hydroxideCatalyst

Procedure

To a solution of N-benzyl-2,3-dihydro-2-(2-methoxyphenyl)-4-pyridone (5.5 g, 18.77 mmol) (which was prepared by the procedures of Yamamoto et al., Tetrahedron, 1993, 49, 1749) in methanol (80 mL) was added Pd(OH)2 (1.7 g) and the resulting suspension was hydrogenated (50 psi) for 20 hours. Pd-C was then filtered off and the crude reaction mixture was concentrated in vacuo to give a residue, which was purified by silica gel flash chromatography (5% MeOH-0.5% NH3♦H2O-94.5% CH2Cl2) to afford the title compound as a solid (1.5 g). 13C NMR (CDCl3, 100 MHz) ) δ: 156.5, 131.4, 128.1, 126.9, 120.8, 110.3, 69.6, 55.3, 53.8, 45.1, 41.7, and 35.6.

Workup

  1. customfor 20 hours
  2. filtrationPd-C was then filtered off
  3. customthe crude reaction mixture
  4. concentrationwas concentrated in vacuo
  5. customto give a residue, which
  6. customwas purified by silica gel flash chromatography (5% MeOH-0.5% NH3♦H2O-94.5% CH2Cl2)

Sources & evidence

ORD record
ord-36353a813680467b9bd0d32687e6a88a
Source dataset
uspto-grants-2001_10
Patent number
US06300316B1

Reaction notes

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