ethyl 1,2,5,6-tetrahydro-3-hydroxy-2-oxopyridine-4-carboxylate → Ethyl 3-hydroxy-2-oxo-1,2-dihydropyridine-4-carboxylate

HRID 880018Notes

Reaction equation

HRID 880018 reaction equation
[OH:1][C:2]1[C:7](=[O:8])[NH:6][CH2:5][CH2:4][C:3]=1[C:9]([O:11][CH2:12][CH3:13])=[O:10]>C1(C)C(C)=CC=CC=1.[Pd]>[OH:1][C:2]1[C:7](=[O:8])[NH:6][CH:5]=[CH:4][C:3]=1[C:9]([O:11][CH2:12][CH3:13])=[O:10]

Participants

4

Reactant 1

HCID 54692116ethyl 1,2,5,6-tetrahydro-3-hydroxy-2-oxopyridine-4-carboxylate

Product 1

HCID 54697099Ethyl 3-hydroxy-2-oxo-1,2-dihydropyridine-4-carboxylateYield 80%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 7237O-XyleneSolvent

Conditions

Temperature
130 °C

Procedure

To a solution of Intermediate 1A (20 g) in xylene (400 mL) was added 10% Pd/C (4 g). The mixture was heated at 130° C. for 24 h. The reaction was filtered through a pad of Celite®. Methanol was used for filtration and washing. The filtrate was concentrated and the residue was purified by ISCO flash chromatography (silica gel, 0-100% EtOAc/hexane) to give Intermediate 1B (15 g, 80% yield).

Workup

  1. filtrationThe reaction was filtered through a pad of Celite®
  2. filtrationMethanol was used for filtration
  3. washwashing
  4. concentrationThe filtrate was concentrated
  5. customthe residue was purified by ISCO flash chromatography (silica gel, 0-100% EtOAc/hexane)

Sources & evidence

ORD record
ord-44f5ff2d37ca45f5ae20743e2d508dcd
Source dataset
uspto-grants-2015_03
Patent number
US08993557B2

Reaction notes

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