Phenylhydrazine → HCID 13712335, compound

HRID 2231209Notes

Reaction equation

HRID 2231209 reaction equation
[Cl:1][C:2]1[CH:11]=[C:10]2[C:5]([CH2:6][CH2:7][CH:8]([CH2:13][C:14]([OH:16])=O)[C:9]2=O)=[CH:4][CH:3]=1.[C:17]1([NH:23][NH2:24])[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1>C(O)C>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]2[CH2:6][CH2:7][CH:8]3[C:9]([C:10]=2[CH:11]=1)=[N:24][N:23]([C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1)[C:14](=[O:16])[CH2:13]3

Participants

4

Reactant 2

HCID 7516PhenylhydrazineHCID 13712334HCID 13712334, compound

Product 1

HCID 13712335HCID 13712335, compoundYield 71%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of 12 g of 7-chloro-1,2,3,4-tetrahydro-1-oxo-2-naphthaleneacetic acid and 8.1 g of phenylhydrazine in 150 ml of ethanol is refluxed under heating for 14 hours. Then the ethanol is distilled off under reduced pressure, 100 ml of acetic acid is added to the residue and the mixture is refluxed under heating for 7 hours. After the acetic acid is distilled off, the residue is extracted with chloroform. The extract is washed with water, dried over magnesium sulfate anhydride and then the chloroform is distilled off to give crystals. The precipitated crystals are collected by filtration and recrystallized from alcohol to give 11.1 g of 9-chloro-2-phenyl-4,4a,5,6-tetrahydrobenzo[h]cinnolin-3(2H)-one as colorless prisms, melting at 120°-122° C.

Workup

  1. temperatureis refluxed
  2. temperatureunder heating for 14 hours
  3. distillationThen the ethanol is distilled off under reduced pressure, 100 ml of acetic acid
  4. additionis added to the residue
  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
  12. customto give crystals
  13. filtrationThe precipitated crystals are collected by filtration
  14. customrecrystallized from alcohol

Sources & evidence

ORD record
ord-2c90a1b2ee7a475c83aeea837f492ee1
Source dataset
uspto-grants-1988_11
Patent number
US04782057

Reaction notes

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