2-Amino-3,4-diethoxycarbonyl-6-phenylpyridine hydrochloride → 3,4-Diethoxycarbonyl-6-phenyl-2-pyridone

HRID 37466Notes

Reaction equation

HRID 37466 reaction equation
Cl.N[C:3]1[C:8]([C:9]([O:11][CH2:12][CH3:13])=[O:10])=[C:7]([C:14]([O:16][CH2:17][CH3:18])=[O:15])[CH:6]=[C:5]([C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)[N:4]=1.N([O-])=[O:26].[Na+]>Cl.O1CCOCC1.O>[CH2:12]([O:11][C:9]([C:8]1[C:3](=[O:26])[NH:4][C:5]([C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)=[CH:6][C:7]=1[C:14]([O:16][CH2:17][CH3:18])=[O:15])=[O:10])[CH3:13]

Participants

6

Reactant 2

HCID 199356132-Amino-3,4-diethoxycarbonyl-6-phenylpyridine hydrochlorideHCID 23668193Sodium Nitrite

Product 1

HCID 199356223,4-Diethoxycarbonyl-6-phenyl-2-pyridone

Reagents, catalysts & solvents 3

HCID 313Hydrochloric AcidSolventHCID 962WaterSolventHCID 312751,4-DioxaneSolvent

Procedure

In a mixture of 90 ml of 2% hydrochloric acid and 60 ml of dioxane was dissolved 3.50 g (10 mmol) of 2-amino-3,4-diethoxycarbonyl-6-phenylpyridine hydrochloride. A solution of 0.83 g (1.2 eq.) of sodium nitrite dissolved in 3 ml of water was added dropwise thereto. The mixture was stirred at room temperature for 4 hours and left standing overnight. The solvent was distilled off. The resulting crystals were collected by filtration with water. The crystals were recrystallized from ethanol, to give pale yellow prisms.

Workup

  1. additionwas added dropwise
  2. waitleft
  3. waitstanding overnight
  4. distillationThe solvent was distilled off
  5. filtrationThe resulting crystals were collected by filtration with water
  6. customThe crystals were recrystallized from ethanol
  7. customto give pale yellow prisms

Sources & evidence

ORD record
ord-3ba45d3f0a9040be8c9e7621a06f83d8
Source dataset
uspto-grants-1995_05
Patent number
US05420275

Reaction notes

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