Sodium Hydroxide → HCID 22097061, compound

HRID 1458834Notes

Reaction equation

HRID 1458834 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-283b92ea8ed4473b95a9416fbcc4944a
Source dataset
uspto-grants-1998_12
Patent number
US05852017

Reaction notes

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