Hydrochloric Acid → 3,4-Diethoxycarbonyl-6-(4-methoxyphenyl)-2-pyridone

HRID 37481Notes

Reaction equation

HRID 37481 reaction equation
N[C:2]1[C:7]([C:8]([O:10][CH2:11][CH3:12])=[O:9])=[C:6]([C:13]([O:15][CH2:16][CH3:17])=[O:14])[CH:5]=[C:4]([C:18]2[CH:23]=[CH:22][C:21]([O:24][CH3:25])=[CH:20][CH:19]=2)[N:3]=1.Cl.[O:27]1CCOCC1.N([O-])=O.[Na+]>O>[CH2:11]([O:10][C:8]([C:7]1[C:2](=[O:27])[NH:3][C:4]([C:18]2[CH:23]=[CH:22][C:21]([O:24][CH3:25])=[CH:20][CH:19]=2)=[CH:5][C:6]=1[C:13]([O:15][CH2:16][CH3:17])=[O:14])=[O:9])[CH3:12]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 312751,4-DioxaneHCID 19935580HCID 19935580, compoundHCID 23668193Sodium Nitrite

Product 1

HCID 199355943,4-Diethoxycarbonyl-6-(4-methoxyphenyl)-2-pyridone

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To 100 mg of 2-amino-3,4-diethoxycarbonyl-6-(4-methoxyphenyl)pyridine were added 2 ml of 1N hydrochloric acid and 5 ml of dioxane, and thereto was added dropwise a solution of 26 mg (1.3 eq.) of sodium nitrite dissolved in 0.5 ml of water under ice-cooling. The mixture was stirred at room temperature overnight. The solvent was distilled off. The residue was neutralized with sodium hydrogencarbonate, followed by extraction with ethyl acetate. The organic layer was washed with a saturated aqueous solution of sodium chloride and dried. The solvent was distilled off. The resulting crude crystals were recrystallized from ethanol.

Workup

  1. temperaturecooling
  2. distillationThe solvent was distilled off
  3. extractionfollowed by extraction with ethyl acetate
  4. washThe organic layer was washed with a saturated aqueous solution of sodium chloride
  5. customdried
  6. distillationThe solvent was distilled off
  7. customThe resulting crude crystals were recrystallized from ethanol

Sources & evidence

ORD record
ord-0393861d553240e4a17a127318d44d8e
Source dataset
uspto-grants-1995_05
Patent number
US05420275

Reaction notes

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