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 1866934Notes

Reaction equation

HRID 1866934 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-one

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, 77w): 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-1468ef567b694eaa88d5b66489c52a2c
Source dataset
uspto-grants-2009_12
Patent number
US07629363B2

Reaction notes

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