Nitric Acid → 4-hydroxy-3-nitro-1-phenylquinolin-2(1H)-one

HRID 462073

Reaction equation

HRID 462073 reaction equation
[OH:1][C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[N:5]([C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)[C:4](=[O:18])[CH:3]=1.[N+:19]([O-])([OH:21])=[O:20]>C(O)(=O)C>[OH:1][C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[N:5]([C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)[C:4](=[O:18])[C:3]=1[N+:19]([O-:21])=[O:20]

Participants

4

Reactant 2

HCID 944Nitric AcidHCID 546761614-Hydroxy-1-phenyl-1,2-dihydroquinolin-2-one

Product 1

HCID 546838884-hydroxy-3-nitro-1-phenylquinolin-2(1H)-one

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

A solution of 4-hydroxy-1-phenyl carbostyril (2.20g.; 0.0093 mole) in glacial acetic acid (10 ml.) was treated rapidly with concentrated nitric acid (2.5 ml. d 1.42) and the mixture heated on a steam bath for 21/2 mins. The red solution deposited a dark yellow solid on cooling which, after dilution with ethanol, was filtered off and washed well with ethanol, m.p. (AcOH -- EtOH) 167° - 169° C. (Found; C, 64.13; H, 3.70; N, 9.85; C15H10N2O4 requires; C, 63.83; H, 3.57; N, 9.92%).

Workup

  1. temperaturethe mixture heated on a steam bath for 21/2 mins
  2. temperatureon cooling which
  3. filtrationafter dilution with ethanol, was filtered off
  4. washwashed well with ethanol
  5. custom(AcOH -- EtOH) 167° - 169° C. (Found; C, 64.13; H, 3.70; N, 9.85; C15H10N2O4 requires; C, 63.83; H, 3.57; N, 9.92%)

Sources & evidence

ORD record
ord-a69f5488a0de4c33a7336ae511963b3d
Source dataset
uspto-grants-1977_12
Patent number
US04065457

Linked notes

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