Acetic Acid → HCID 21189949, compound

HRID 1600764Notes

Reaction equation

HRID 1600764 reaction equation
[CH3:1][O:2][C:3]1[C:12]([O:13][CH3:14])=[CH:11][C:10]2[C:5](=[N:6][C:7](=[O:16])[C:8](=[O:15])[N:9]=2)[CH:4]=1.[N+]([O-])(O)=O.[C:21]([OH:24])(=[O:23])[CH3:22]>>[C:21]([O:24][C:4]1[C:5]2[C:10]([CH:11]=[C:12]([O:13][CH3:14])[C:3]=1[O:2][CH3:1])=[N:9][C:8](=[O:15])[C:7](=[O:16])[N:6]=2)(=[O:23])[CH3:22]

Participants

4

Reactant 3

HCID 176Acetic AcidHCID 944Nitric AcidHCID 21189996HCID 21189996, compound

Product 1

HCID 21189949HCID 21189949, compoundYield 54%

Procedure

6,7-Dimethoxy-2,3-quinoxalinedione (45) (222 mg, 1.0 mmol) was dissolved in glacial acetic acid (10 mL) at 100° C. (oil bath). The oil bath was removed and fuming nitric acid (53 μL, 1.2 mmol; Baker) was added dropwise to the solution. The reaction mixture was then stirred at room temperature for 24 h. The mixture was filtered and washed with water to give a white solid, giving 150 mg (54%) of the title compound; mp 321-322° C.; 1H NMR (DMSO-d6, 300 MHz) δ 2.300 (s, 3H), 3.619 (s, 3H), 3.746 (s, 3H), 6.661 (s, 1H), 11.700 (s, 1H), 11.832 (s, 1H). EIMS m/e 280 (M+, 30), 238 (100). Anal. Calcd for C12H12N2O6 : C, 51.43; H, 4.32; N, 10.00. Found: C, 51.29; H, 4.04; N, 9.90. (HPLC purity>99%).

Workup

  1. customThe oil bath was removed
  2. filtrationThe mixture was filtered
  3. washwashed with water
  4. customto give a white solid

Sources & evidence

ORD record
ord-9f9db0fa92314745ac84cb12c533d25d
Source dataset
uspto-grants-1999_11
Patent number
US05977107

Reaction notes

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