Phenylhydrazine → HCID 21286379, compound

HRID 2231216Notes

Reaction equation

HRID 2231216 reaction equation
[N+:1]([C:4]1[CH:13]=[C:12]2[C:7]([CH2:8][CH2:9][CH:10]([CH2:15][C:16]([OH:18])=O)[C:11]2=O)=[CH:6][CH:5]=1)([O-:3])=[O:2].[C:19]1([NH:25][NH2:26])[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1>C(O)C>[N+:1]([C:4]1[CH:5]=[CH:6][C:7]2[CH2:8][CH2:9][CH:10]3[C:11]([C:12]=2[CH:13]=1)=[N:26][N:25]([C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1)[C:16](=[O:18])[CH2:15]3)([O-:3])=[O:2]

Participants

4

Reactant 2

HCID 7516PhenylhydrazineHCID 21286380HCID 21286380, compound

Product 1

HCID 21286379HCID 21286379, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution of 7-nitro-1,2,3,4-tetrahydro-1-oxo-2-naphthaleneacetic acid and phenylhydrazine in ethanol is refluxed under heating for 10 hours. The ethanol is distilled off and to the residue is added acetic acid and then the resulting mixture is refluxed under heating for 8 hours. After the acetic acid is distilled off, the mixture is extracted with chloroform and the extract is washed with water. After drying over magnesium sulfate anhydride, the chloroform is distilled off to give 9-nitro-2-phenyl-4,4a,5,6-tetrahydrobenzo[h]cinnolin-3(2H)-one.

Workup

  1. temperatureunder heating for 10 hours
  2. distillationThe ethanol is distilled off and to the residue
  3. additionis added acetic acid
  4. temperaturethe resulting mixture is refluxed
  5. temperatureunder heating for 8 hours
  6. distillationAfter the acetic acid is distilled off
  7. extractionthe mixture is extracted with chloroform
  8. washthe extract is washed with water
  9. dry with materialAfter drying over magnesium sulfate anhydride
  10. distillationthe chloroform is distilled off

Sources & evidence

ORD record
ord-781c449de9ae4e97ad5b1fb0373e7269
Source dataset
uspto-grants-1988_11
Patent number
US04782057

Reaction notes

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