Acetic Acid → 5-Nitroquinoline 1-oxide

HRID 2182652Notes

Reaction equation

HRID 2182652 reaction equation
[N+:1]([C:4]1[CH:13]=[CH:12][CH:11]=[C:10]2[C:5]=1[CH:6]=[CH:7][CH:8]=[N:9]2)([O-:3])=[O:2].[Na+].[Cl-].C(O)(=[O:18])C>OO>[N+:1]([C:4]1[CH:13]=[CH:12][CH:11]=[C:10]2[C:5]=1[CH:6]=[CH:7][CH:8]=[N+:9]2[O-:18])([O-:3])=[O:2]

Participants

5

Reactant 3

HCID 176Acetic AcidHCID 5234Sodium ChlorideHCID 118295-Nitroquinoline

Product 1

HCID 820855-Nitroquinoline 1-oxide

Reagents, catalysts & solvents 1

HCID 784Hydrogen PeroxideSolvent

Procedure

A solution of 25.5 g (146 mmol) of 5-nitroquinoline in 544 ml of acetic acid and 272 ml of 30% aqueous H2O2 solution are heated for 100 minutes to 62-69° C. The reaction mixture is poured onto saturated NaCl solution and extracted with ethyl acetate. The combined extracts are concentrated by evaporation to about 50 ml with the addition of toluene. Column chromatography on silica gel with ethyl acetate-MeOH yields 12.3 g of the product as a yellow solid.

Workup

  1. extractionextracted with ethyl acetate
  2. concentrationThe combined extracts are concentrated by evaporation to about 50 ml with the addition of toluene

Sources & evidence

ORD record
ord-922882d6ae3c4fe99f34da7b5de3b37b
Source dataset
uspto-grants-2005_05
Patent number
US06897224B2

Reaction notes

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