Nitric Acid → HCID 178514693, compound

HRID 1165826Notes

Reaction equation

HRID 1165826 reaction equation
[OH:1][C:2]1[C:3]([OH:20])=[N:4][C:5]2[CH:6]=[CH:7][C:8]3[C:15]([S:16](=[O:19])(=[O:18])[NH2:17])=[CH:14][CH:13]=[CH:12][C:9]=3[C:10]=2[N:11]=1.[N+:21]([O-])([OH:23])=[O:22]>S(=O)(=O)(O)O>[OH:1][C:2]1[C:3]([OH:20])=[N:4][C:5]2[CH:6]=[C:7]([N+:21]([O-:23])=[O:22])[C:8]3[C:15]([S:16](=[O:18])(=[O:19])[NH2:17])=[CH:14][CH:13]=[CH:12][C:9]=3[C:10]=2[N:11]=1

Participants

4

Reactant 2

HCID 944Nitric AcidHCID 178514692HCID 178514692, compound

Product 1

HCID 178514693HCID 178514693, compoundYield 61%

Reagents, catalysts & solvents 1

HCID 1118Sulfuric AcidSolvent

Procedure

To a solution of 1,0 g (3,4 mmol) 2,3-dihydroxy-7-sulphamoylbenzo[f]quinoxaline in 25 ml concentrated sulfuric acid was added at 0° C. 0,15 ml 100% nitric acid. Stirring was continued at 0° C. for 30 min, and then the mixture was poured into 100 ml ice-water to give a precipitate. The crude product was recrystallized (dimethylformamide-water) to give 0,7 g (61%) 2,3-dihydroxy-6-nitro-7-sulphamoyl-benzo[f]quinoxaline, m.p. 360° C. NMR (DMSO-d6): 12,4 (1H, broad s), 12,3 (1H, broad s), 8.7 (1H, d), 8.5 (1H,d), 8.17 (1H,s), 7.9 (1H,t), 7.4 (2H, broad s).

Workup

  1. customto give a precipitate
  2. customThe crude product was recrystallized (dimethylformamide-water)

Sources & evidence

ORD record
ord-d11b857e329948e2b618022c9c913761
Source dataset
uspto-grants-1990_03
Patent number
US04912108

Reaction notes

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