Nitric Acid → HCID 9816093, compound

HRID 1781029Notes

Reaction equation

HRID 1781029 reaction equation
[CH3:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][C:11]=1[CH3:12])[NH:8][C:7](=[O:13])[C:6](=[O:14])[NH:5]2.[N+:15]([O-])([OH:17])=[O:16]>OS(O)(=O)=O>[CH3:12][C:11]1[C:10]([N+:15]([O-:17])=[O:16])=[C:9]2[C:4](=[CH:3][C:2]=1[CH3:1])[NH:5][C:6](=[O:14])[C:7](=[O:13])[NH:8]2

Participants

4

Reactant 2

HCID 944Nitric AcidHCID 2476706,7-Dimethyl-2,3-quinoxalinediol

Product 1

HCID 9816093HCID 9816093, compoundYield 60%

Reagents, catalysts & solvents 1

HCID 1118Sulfuric AcidSolvent

Procedure

To a solution of 1.90 g (10.0 mmol) of 6,7-dimethyl-1,4-dihydroquinoxaline-2,3-dione in 25 mL of H2SO4 (97%) kept in an ice bath was added dropwise 1.2 mL of HNO3 (69-70%) and the solution was stirred at room temperature for 48 h. It was poured into 300 mL of ice-water and stirred for 10 min. The mixture was filtered, washed with water, and dried to leave a yellow solid 1.40 g (60%). The solid was purified by DMSO/H2O precipitation followed by NaOH/HCl precipitation to leave 0.85 g of a yellow solid; mp>250° C.; 1H NMR (DMSO-d6), 2.079 (s,3), 2.246 (s,3), 7.048 (s,1), 11.770 (s,1), 12.030 (s,1). HRMS calcd. for C10H9N3O4 235.0588; found 235.0584.

Workup

  1. stirringstirred for 10 min
  2. filtrationThe mixture was filtered
  3. washwashed with water
  4. customdried

Sources & evidence

ORD record
ord-b9209e1cd3964563a3a61efb57e33278
Source dataset
uspto-grants-1997_05
Patent number
US05631373

Reaction notes

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