Phenylhydrazine → HCID 21286394, compound

HRID 2231212Notes

Reaction equation

HRID 2231212 reaction equation
[F:1][C:2]([F:19])([F:18])[C:3]1[CH:12]=[C:11]2[C:6]([CH2:7][CH2:8][CH:9]([CH2:14][C:15]([OH:17])=O)[C:10]2=O)=[CH:5][CH:4]=1.[C:20]1([NH:26][NH2:27])[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1>C(O)C>[C:20]1([N:26]2[C:15](=[O:17])[CH2:14][CH:9]3[C:10]([C:11]4[CH:12]=[C:3]([C:2]([F:1])([F:19])[F:18])[CH:4]=[CH:5][C:6]=4[CH2:7][CH2:8]3)=[N:27]2)[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1

Participants

4

Reactant 2

HCID 7516PhenylhydrazineHCID 21286384HCID 21286384, compound

Product 1

HCID 21286394HCID 21286394, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

After a mixture of 7-trifluoromethyl-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. To the residue is added acetic acid and the mixture is refluxed under heating for 7 hours. After the acetic acid is distilled off, the residue is extracted with chloroform and the extract is washed with water and dried over magnesium sulfate anhydride. The chloroform is distilled off to give 2-phenyl-9-trifluoromethyl-4,4a,5,6-tetrahydrobenzo[h]cinnolin-3(2H)-one.

Workup

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

Sources & evidence

ORD record
ord-1b6887008fd142e1a95e52c971b70d2b
Source dataset
uspto-grants-1988_11
Patent number
US04782057

Reaction notes

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