Sulfuric Acid → HCID 22097097, compound

HRID 1458831Notes

Reaction equation

HRID 1458831 reaction equation
N[C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][C:11]=1[N+:12]([O-:14])=[O:13])[N:8]([CH2:15][CH3:16])[C:7](=[O:17])[C:6](=[O:18])[NH:5]2.N([O-])=O.[Na+].S(=O)(=O)(O)O>C(O)(=O)C.C(O)C.[Cu-]=O>[CH2:15]([N:8]1[C:9]2[C:4](=[CH:3][CH:2]=[C:11]([N+:12]([O-:14])=[O:13])[CH:10]=2)[NH:5][C:6](=[O:18])[C:7]1=[O:17])[CH3:16]

Participants

7

Reactant 3

HCID 1118Sulfuric AcidHCID 22097137HCID 22097137, compoundHCID 23668193Sodium Nitrite

Product 1

HCID 22097097HCID 22097097, compoundYield 64%

Reagents, catalysts & solvents 3

HCID 178419072HCID 178419072, compoundCatalystHCID 176Acetic AcidSolventHCID 702EthanolSolvent

Procedure

14.2 g (57 mmol) of 6-amino-1-ethyl-7-nitro-2,3(1H,4H)-quinoxalinedione (Example 30 a) were suspended in 340 ml of acetic acid. To this was added dropwise at 10°-20° C. a solution of 5.1 g (74 mmol) of sodium nitrite and 80 ml of concentrated sulfuric acid. The mixture was stirred for a further 30 minutes and then this solution was added dropwise to another suspension of 16.3 g (114 mmol) of copper(I) oxide in 140 ml ethanol. The mixture was stirred for a further 10 minutes and then poured into 1 l of ice-water. After filtration, the filtrate was extracted with methylene chloride and the organic phase was dried and concentrated under reduced pressure to yield 8.5 g (64%) of the product.

Workup

  1. stirringThe mixture was stirred for a further 10 minutes
  2. filtrationAfter filtration
  3. extractionthe filtrate was extracted with methylene chloride
  4. customthe organic phase was dried
  5. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-b0b5e3acbe444e19a886f57b34f20f5e
Source dataset
uspto-grants-1998_12
Patent number
US05852017

Reaction notes

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