Phenylhydrazine → Hydrazine

HRID 1600032Notes

Reaction equation

HRID 1600032 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>[NH2:31][NH2:32].[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

5

Reactant 2

HCID 7516PhenylhydrazineHCID 178418399HCID 178418399, compound

Product 2

HCID 9321HydrazineHCID 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) was 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 thephenyl 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 roomtemperature. Filtration gave the title compound (1.01 g, 58%) as a tan powder, mp 368° C. (decomp.); MS(CI): 351 (M+H). Analysis for C17H10N4O5 : Calculated: C, 58.30; H, 2.88; N, 16.00; Found: C, 58.21; H, 3.07; N, 16.15; NMR: 8.91 (d, J=2.76 Hz, 1H), 8.60 (dd, J=2.76, 9.18 Hz, 1H), 8.06 (d, J=9.18 Hz, 1H,), 7.18 (t, J=7.23 Hz, 2H), 6.82 (m, 3H).

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-c90a6d3db70645e2b0247c96c8b561ca
Source dataset
uspto-grants-1998_04
Patent number
US05744471

Reaction notes

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