Oxalic acid dihydrate → 1-Methyl-6-nitro-1,4-dihydroquinoxaline-2,3-dione

HRID 1494329Notes

Reaction equation

HRID 1494329 reaction equation
[NH2:1][C:2]1[CH:9]=[C:8]([N+:10]([O-:12])=[O:11])[CH:7]=[CH:6][C:3]=1[NH:4][CH3:5].O.O.[C:15](O)(=[O:19])[C:16](O)=[O:17]>Cl>[CH3:5][N:4]1[C:3]2[C:2](=[CH:9][C:8]([N+:10]([O-:12])=[O:11])=[CH:7][CH:6]=2)[NH:1][C:16](=[O:17])[C:15]1=[O:19]

Participants

4

Reactant 2

HCID 61373Oxalic acid dihydrateHCID 34200251-N-methyl-4-nitrobenzene-1,2-diamine

Product 1

HCID 37996491-Methyl-6-nitro-1,4-dihydroquinoxaline-2,3-dioneYield 78%

Reagents, catalysts & solvents 1

HCID 313Hydrochloric AcidSolvent

Conditions

Temperature
25 °C

Procedure

A mixture of 1.0 g (5.9 mmol) 2-amino-4-nitro-N-methylaniline and 1.5 g (11.9 mmol) oxalic acid dihydrate in 50 ml 4N hydrochloric acid was refluxed for 3 h. After cooling to 25° C., the precipitate was filtered off and washed with water. The crude product was recrystallized (dimethylformamide-water) to give 1.0 g (78%) of 1-methyl-6-nitroquinoxaline-2.3-(1H,4H)-dione. M.p. 356° C. NMR (DMSO-d6): 12.2 (1H, broad s), 7.9 (1H, d), 7.8 (1H, s), 7.4 (1H, d), 3.47 (3H, s).

Workup

  1. temperaturewas refluxed for 3 h
  2. filtrationthe precipitate was filtered off
  3. washwashed with water
  4. customThe crude product was recrystallized (dimethylformamide-water)

Sources & evidence

ORD record
ord-23aff0a8cc8344a3b8f44fbd67f736df
Source dataset
uspto-grants-1991_06
Patent number
US05026704

Reaction notes

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