Phenylhydrazine → HCID 178515136, compound

HRID 1977204Notes

Reaction equation

HRID 1977204 reaction equation
[N+:1]([C:4]1[CH:5]=[C:6]2[C:11](=[CH:12][CH:13]=1)[N:10]=[C:9]([C:14]([O:16]CC)=O)[C:8]([C:19]([O:21]CC)=O)=[C:7]2[OH:24])([O-:3])=[O:2].[C:25]1([NH:31][NH2:32])[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1>C(O)C>[OH:16][C:14]1[C:9]2[NH:10][C:11]3[CH:12]=[CH:13][C:4]([N+:1]([O-:3])=[O:2])=[CH:5][C:6]=3[C:7](=[O:24])[C:8]=2[C:19](=[O:21])[N:31]([C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=2)[N:32]=1

Participants

4

Reactant 2

HCID 7516PhenylhydrazineHCID 178418399HCID 178418399, compound

Product 1

HCID 178515136HCID 178515136, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent2×

Procedure

To a stirred suspension of diethyl 6-nitro-4-hydroxy-quinoline-2,3-dicarboxylate (1.670 g, 5.00 mM) in ethanol (30 mL) vas added phenyl hydrazine (3.44 mL, 35.00 mM) to give a deep red solution. The solution was heated to reflux for 1 hour and concentrated to about 15 mL. Continued heating gave a thick suspension which was diluted with ethanol (5 mL) and refluxed for 16 additional hours. The mixture was cooled to room temperature and filtered to give the phenyl hydrazine salt of the title compound as a tan solid. This material was refluxed in glacial acetic acid (25 mL) for 2 hours and cooled to room temperature. Filtration gave the title compound (1.01 g, 58%) as a tan powder, mp 368° C. (decomp.); MS(CI): 351 (M+H).

Workup

  1. customto give a deep red solution
  2. temperatureThe solution was heated
  3. temperatureto reflux for 1 hour
  4. concentrationconcentrated to about 15 mL
  5. temperatureContinued heating
  6. customgave a thick suspension which
  7. temperaturerefluxed for 16 additional hours
  8. filtrationfiltered

Sources & evidence

ORD record
ord-d43adf06d1384a7db139afd98f486e26
Source dataset
uspto-grants-2001_05
Patent number
US06232313B1

Reaction notes

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