Potassium Nitrate → HCID 178526421, compound

HRID 1793283Notes

Reaction equation

HRID 1793283 reaction equation
[N+:1]([O-:4])([O-])=[O:2].[K+].[Cl:6][C:7]1[CH:8]=[C:9]2[C:14](=[CH:15][CH:16]=1)[N:13]=[C:12]([OH:17])[C:11]([OH:18])=[N:10]2>S(=O)(=O)(O)O>[Cl:6][C:7]1[CH:8]=[C:9]2[C:14](=[CH:15][C:16]=1[N+:1]([O-:4])=[O:2])[N:13]=[C:12]([OH:17])[C:11]([OH:18])=[N:10]2

Participants

4

Reactant 2

HCID 24434Potassium NitrateHCID 178517169HCID 178517169, compound

Product 1

HCID 178526421HCID 178526421, compoundYield 88%

Reagents, catalysts & solvents 1

HCID 1118Sulfuric AcidSolvent

Procedure

Finely powdered potassium nitrate (1.01 g, 10 mmol) is added during 5 min. to a stirred solution of 6-chloro-2,3-dihydroxyquinoxaline (1.97 g, 10 mmol) in 50 ml of concentrated sulfuric acid at 0° C. After 1 h, the ice bath was removed and stirring continued for 2.5 h at room temperature. The mixture is poured into 200 ml of ice/water and the precipitate is isolated, washed with water, ethanol, and ether. The product is dissolved in 70 ml of hot 2N sodium hydroxide, filtered while hot, and reprecipitated with concentrated hypochloric acid to give 2.12 g (88%) of pure title compound. 3H-NMR (DMSO-d6): δ 7.23 (s, 1H, H-5); δ 7.82 (s, 1H, h-8); δ 12.1 (broad s, 2H, 2NH).

Workup

  1. customthe ice bath was removed
  2. waitcontinued for 2.5 h at room temperature
  3. additionThe mixture is poured into 200 ml of ice/water
  4. customthe precipitate is isolated
  5. washwashed with water, ethanol, and ether
  6. dissolutionThe product is dissolved in 70 ml of hot 2N sodium hydroxide
  7. filtrationfiltered while hot, and
  8. customreprecipitated with concentrated hypochloric acid

Sources & evidence

ORD record
ord-d389543dfca3403984fc379dfada1957
Source dataset
uspto-grants-2006_07
Patent number
US07081346B2

Reaction notes

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