N-Benzyl-3-benzyloxy-2-pyridone → HCID 22339931, compound

HRID 1711202Notes

Reaction equation

HRID 1711202 reaction equation
[CH2:1]([N:8]1[CH:13]=[CH:12][CH:11]=[C:10]([O:14]CC2C=CC=CC=2)[C:9]1=[O:22])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[H][H]>CO.[Pd]>[CH2:1]([N:8]1[CH:13]=[CH:12][CH:11]=[C:10]([OH:14])[C:9]1=[O:22])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 2

HCID 90335N-Benzyl-3-benzyloxy-2-pyridoneHCID 178418361HCID 178418361, compound

Product 1

HCID 22339931HCID 22339931, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

1-Benzyl-3-benzyloxy-1H-pyridin-2-one (Ghosh et al, J. Org. Chem. 1989, 54, 5073) is dissolved in anhydrous methanol (10 mL) and to the thoroughly degassed solution is added a catalytic amount of Pd—C (0.1%). The mixture is hydrogenated under a balloon of hydrogen, until all the starting material is consumed. At the completion, the solution is filtered through Celite™. The solvent is removed in vacuo, and the residue is washed with ether, to afford the desired product. 1H NMR (300 MHz, CDCl3) δ 5.15 (s, 2H), 6.14 (t, J=7.2 Hz, 1H); 6.71 (m, 1H), 7.31 (m, 6H), 9.07 (s, 1H). B. General Procedure for the Three Component Coupling Between Pyridones, Formaldehyde and Amines:

Workup

  1. customis consumed
  2. filtrationAt the completion, the solution is filtered through Celite™
  3. customThe solvent is removed in vacuo
  4. washthe residue is washed with ether

Sources & evidence

ORD record
ord-61207027204a420b9700d839aa8b49a2
Source dataset
uspto-grants-2010_09
Patent number
US07790748B2

Reaction notes

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