Nitric Acid → 6-Bromo-4-hydroxy-3-nitroquinolin-2(1H)-one

HRID 462060Notes

Reaction equation

HRID 462060 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[NH:8][C:7](=[O:12])[CH:6]=[C:5]2[OH:13].[N+:14]([O-])([OH:16])=[O:15]>C(O)(=O)C>[Br:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[NH:8][C:7](=[O:12])[C:6]([N+:14]([O-:16])=[O:15])=[C:5]2[OH:13]

Participants

4

Reactant 2

HCID 944Nitric AcidHCID 546894466-Bromo-4-hydroxyquinolin-2(1H)-one

Product 1

HCID 546964876-Bromo-4-hydroxy-3-nitroquinolin-2(1H)-one

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Conditions

Temperature
100 °C

Procedure

A suspension of 6-bromo-4-hydroxycarbostyril (2.23g, 0.0093 mole) in glacial acetic acid (15 ml) was swirled during the addition of concentrated nitric acid (2.5 ml, d, 1.42). On heating at 100° C for several minutes a thick yellow solid separated. After cooling, ethanol (40 ml) was added and the mixture filtered and the solid washed free of nitric acid with ethanol. Drying in vacuo over P2O5 gave the title compound, m.p. 231°-4° C (d). (Found; C, 37.83; H, 1.74; N, 9.77; Br, 28.33; C9H5N2BrO4 requires; C, 37.92; H, 1.77; N, 9.83; Br, 28.03%).

Workup

  1. customseparated
  2. temperatureAfter cooling
  3. additionethanol (40 ml) was added
  4. filtrationthe mixture filtered
  5. washthe solid washed free of nitric acid with ethanol
  6. dry with materialDrying in vacuo over P2O5

Sources & evidence

ORD record
ord-e3523cad4877469593050ce2abb904f9
Source dataset
uspto-grants-1977_12
Patent number
US04065457

Reaction notes

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