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

HRID 1658092Notes

Reaction equation

HRID 1658092 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. 213°-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-949a4af1852647eb9000bffd910d3553
Source dataset
uspto-grants-1976_06
Patent number
US03962445

Reaction notes

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