3-(benzyloxy)-N,1,6-trimethyl-4-oxo-1,4-dihydropyridine-2-carboxamide → 3-Hydroxy-N,1,6-trimethyl-4-oxo-1,4-dihydropyridine-2-carboxamide

HRID 1016687Notes

Reaction equation

HRID 1016687 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]([NH:20][CH3:21])=[O:19])C1C=CC=CC=1.[H][H]>C(O)C.[OH-].[OH-].[Pd+2]>[OH:8][C:9]1[C:14](=[O:15])[CH:13]=[C:12]([CH3:16])[N:11]([CH3:17])[C:10]=1[C:18]([NH:20][CH3:21])=[O:19]

Participants

5

Reactant 2

HCID 114716923-(benzyloxy)-N,1,6-trimethyl-4-oxo-1,4-dihydropyridine-2-carboxamideHCID 178418361HCID 178418361, compound

Product 1

HCID 546900063-Hydroxy-N,1,6-trimethyl-4-oxo-1,4-dihydropyridine-2-carboxamideYield 100.4%

Reagents, catalysts & solvents 2

HCID 9942167Palladium hydroxideCatalystHCID 702EthanolSolvent

Procedure

Pd(OH)2 on charcoal (0.2 g) was added to a solution of 3-(benzyloxy)-N,1,6-trimethyl-4-oxo-1,4-dihydropyridine-2-carboxamide (1.25 g, 4.366 mmol) in ethanol (120 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 (3×25 ml). The Celite cake was further stirred with ethanol (100 ml) and then filtered through Celite. The combined ethanol filtrate was evaporated to give a solid (0.86 g, quantitative yield). Melting point: >250° C. H-NMR (CDCl3; DMSO-d6 [2:1]) δ: 1.81 (s, 3H, Me), 2.34 (d, 3H, NHMe), 3.01 (s, 3H, NMe), 5.67 (s, 1H, CH), 7.88 (s, 1H, NH). Elemental Analysis: Calc. C, 55.09; H, 6.6; N, 14.28. Found. C, 54.67; H, 6.31; N, 14.12.

Workup

  1. customThe Pd(OH)2 was removed by filtration through Celite
  2. washthe Celite cake was washed with ethanol (3×25 ml)
  3. filtrationfiltered through Celite
  4. customThe combined ethanol filtrate was evaporated

Sources & evidence

ORD record
ord-fb39aabf0195453d814829d99bfba66c
Source dataset
uspto-grants-2002_11
Patent number
US06476229B1

Reaction notes

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