Sodium Hydroxide → HCID 22097061, compound

HRID 861496Notes

Reaction equation

HRID 861496 reaction equation
C([NH:4][C:5]1[CH:14]=[C:13]2[C:8]([NH:9][C:10](=[O:18])[C:11](=[O:17])[N:12]2[CH2:15][CH3:16])=[CH:7][CH:6]=1)(=O)C.[N+:19]([O-])([O-:21])=[O:20].[Na+].[OH-].[Na+].C(=O)(O)[O-].[Na+]>S(=O)(=O)(O)O>[NH2:4][C:5]1[CH:14]=[C:13]2[C:8]([NH:9][C:10](=[O:18])[C:11](=[O:17])[N:12]2[CH2:15][CH3:16])=[CH:7][C:6]=1[N+:19]([O-:21])=[O:20]

Participants

6

Reactant 4

HCID 14798Sodium HydroxideHCID 24268Sodium NitrateHCID 516892Sodium BicarbonateHCID 22097068HCID 22097068, compound

Product 1

HCID 22097061HCID 22097061, compoundYield 23%

Reagents, catalysts & solvents 1

HCID 1118Sulfuric AcidSolvent

Procedure

5.2 g (21 mmol) of 7-acetamido-1-ethyl-2,3(1H,4H)-quinoxalinedione were dissolved in 75 ml of concentrated sulfuric acid and, at 0°-5° C., 2 g (23 mmol) of sodium nitrate were added. The mixture was stirred at 0°-5° C. for 2 h and then poured into ice-water and stirred at room temperature for 16 h. The mixture was then neutralized with dilute sodium hydroxide solution and sodium bicarbonate solution and concentrated under reduced pressure. The residue was extracted with dimethylformamide and then the organic phase was concentrated anew. The residue was purified on silica gel (mobile phase: toluene/acetone/acetic acid=10:10:1) to yield 1.2 g (23%) of the product.

Workup

  1. stirringstirred at room temperature for 16 h
  2. concentrationconcentrated under reduced pressure
  3. extractionThe residue was extracted with dimethylformamide
  4. concentrationthe organic phase was concentrated anew
  5. customThe residue was purified on silica gel (mobile phase: toluene/acetone/acetic acid=10:10:1)

Sources & evidence

ORD record
ord-105ba34a16254a4bb0bab616c6d7f2cf
Source dataset
uspto-grants-1998_02
Patent number
US05714489

Reaction notes

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