1-Cyclohexyl-4-hydroxy-2,5-dimethyl-6-oxo-1,6-dihydropyridine-3-carboxylic acid → 1-cyclohexyl-4-hydroxy-3,6-dimethyl-1H-pyridin-2-one

HRID 1831949Notes

Reaction equation

HRID 1831949 reaction equation
[CH:1]1([N:7]2[C:12](=[O:13])[C:11]([CH3:14])=[C:10]([OH:15])[C:9](C(O)=O)=[C:8]2[CH3:19])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1>Cl.O>[CH:1]1([N:7]2[C:8]([CH3:19])=[CH:9][C:10]([OH:15])=[C:11]([CH3:14])[C:12]2=[O:13])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6]1

Participants

4

Reactant 1

HCID 547241921-Cyclohexyl-4-hydroxy-2,5-dimethyl-6-oxo-1,6-dihydropyridine-3-carboxylic acid

Product 1

HCID 547241911-cyclohexyl-4-hydroxy-3,6-dimethyl-1H-pyridin-2-oneYield 158.6%

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolventHCID 962WaterSolvent

Procedure

A solution of 1-cyclohexyl-4-hydroxy-2,5-dimethyl-6-oxo-1,6-dihydropyridine-3-carboxylic acid (0.15 g, 0.57 mmol) in concentrated HCl (5 mL) was heated at reflux for 4 h. The reaction mixture was cooled to room temperature, diluted with water and washed with EtOAc. The organic solution was washed with brine, dried (MgSO4), filtered and concentrated under reduced pressure to give 1-cyclohexyl-4-hydroxy-3,6-dimethyl-1H-pyridin-2-one as a white solid (0.2 g, 77%): 1H NMR (300 MHz, DMSO-d6) δ 9.81 (s, 1H), 5.73 (s, 1H), 3.95-3.75 (m, 1H), 2.80-2.55 (m, 2H), 2.25 (s, 3H), 1.85-1.40 (m, 5H), 1.72 (s, 3H), 1.38-1.05 (m, 3H).

Workup

  1. temperatureat reflux for 4 h
  2. washwashed with EtOAc
  3. washThe organic solution was washed with brine
  4. dry with materialdried (MgSO4)
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-5ad9ef06e6df4c7a8acae997b5da4302
Source dataset
uspto-grants-2006_06
Patent number
US07067540B2

Reaction notes

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