Nitric Acid → 4-Hydroxy-3-nitro-2(1H)-quinolinone
Reaction equation
[OH:1][C:2]1[CH:11]=[C:10]([OH:12])[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[N:3]=1.[N+:13]([O-])([OH:15])=[O:14].O>C(O)(=O)C>[N+:13]([C:11]1[C:2](=[O:1])[NH:3][C:4]2[C:9]([C:10]=1[OH:12])=[CH:8][CH:7]=[CH:6][CH:5]=2)([O-:15])=[O:14]Participants
5
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 90 °C
Procedure
To a mixture of 1.45 g (9.00 mmol) of 2,4-dihydroxyquinoline (Aldrich) in 10 mL of glacial acetic acid was added 2.5 mL of HNO3 (69-71%). The mixture was heated at 90° C. for 5 min to become a red solution, then a precipitate was observed in the solution. The mixture was cooled to room temperature, then was added 40 mL of water and the mixture was stirred for 20 min. The mixture was filtered and washed with water, dried to leave 1.54 g (83%) of title compound as a yellow solid, mp 216° C. (decomposed, lit: Buckle, D. R., et al., J. Med. Chem. 18:726-732 (1975), 216° C.). 1H NMR (CDCl3 +DMSO-d6), 7.013 (t, 1, J=7.5), 7.105 (d, 1, J=7.5), 7.396 (t, 1, J=7.2), 7.877 (d, 1, 7.8), 11.72 (mb 1).
Workup
- temperatureThe mixture was cooled to room temperature
- filtrationThe mixture was filtered
- washwashed with water
- customdried
Sources & evidence
- ORD record
- ord-07f31868202f4e61beade3e11b6dc67d
- Source dataset
- uspto-grants-1997_04
- Patent number
- US05622965
Reaction notes
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