3-(Benzyloxy)-N,N-diethyl-1,6-dimethyl-4-oxo-1,4-dihydropyridine-2-carboxamide → N,N-Diethyl-3-hydroxy-1,6-dimethyl-4-oxo-1,4-dihydropyridine-2-carboxamide

HRID 2230916Notes

Reaction equation

HRID 2230916 reaction equation
C([O:8][C:9]1[C:14](=[O:15])[CH:13]=[C:12]([CH3:16])[N:11]([CH3:17])[C:10]=1[C:18]([N:20]([CH2:23][CH3:24])[CH2:21][CH3:22])=[O:19])C1C=CC=CC=1.[H][H]>C(O)C.[OH-].[OH-].[Pd+2]>[CH2:23]([N:20]([CH2:21][CH3:22])[C:18]([C:10]1[N:11]([CH3:17])[C:12]([CH3:16])=[CH:13][C:14](=[O:15])[C:9]=1[OH:8])=[O:19])[CH3:24]

Participants

5

Reactant 2

HCID 120106513-(Benzyloxy)-N,N-diethyl-1,6-dimethyl-4-oxo-1,4-dihydropyridine-2-carboxamideHCID 178418361HCID 178418361, compound

Product 1

HCID 54704399N,N-Diethyl-3-hydroxy-1,6-dimethyl-4-oxo-1,4-dihydropyridine-2-carboxamideYield 94%

Reagents, catalysts & solvents 2

HCID 9942167Palladium hydroxideCatalystHCID 702EthanolSolvent

Procedure

Pd(OH)2 on charcoal (0.1 g) was added to a solution of 3-(benzyloxy)-N,N-diethyl-1,6-dimethyl-4-oxo-1,4-dihydropyridine-2-carboxamide(1.0 g, 3.05 mmol) in ethanol (100 ml) under nitrogen. The mixture was hydrogenated at 50 psi hydrogen for 4 hrs. The Pd(OH)2 was removed by filtration through Celite and the Celite cake was washed with ethanol (3×10 ml). The ethanol filtrate was evaporated to give a slightly red solid (0.66 g, 94%). Melting point: 128 to 130° C. H-NMR (CDCl3) σδ: 1.19 (t, J=7.11 Hz, 3H, Me), 1.30 (t, J=7.00 Hz, 3H, Me), 2.36 (s, 3H, Me), 3.36 (m, 2H, CH2), 3.38 (s, 3H, NMe), 3.64 (q, J=6.90 Hz, 2H, CH2), 6.35 (s, 1H, CH), Mass spect. 239 (M+1).

Workup

  1. customThe Pd(OH)2 was removed by filtration through Celite
  2. washthe Celite cake was washed with ethanol (3×10 ml)
  3. customThe ethanol filtrate was evaporated

Sources & evidence

ORD record
ord-7482afb95ab7443384692eef0ca6dd51
Source dataset
uspto-grants-2002_07
Patent number
US06426418B1

Reaction notes

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