Phenylhydrazine → HCID 13712337, compound

HRID 2231211Notes

Reaction equation

HRID 2231211 reaction equation
O=[C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[CH2:5][CH2:4][C:3]1=[CH:12][C:13]([OH:15])=O.[C:16]1([NH:22][NH2:23])[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1>C(O)C>[C:16]1([N:22]2[C:13](=[O:15])[CH:12]=[C:3]3[C:2]([C:11]4[CH:10]=[CH:9][CH:8]=[CH:7][C:6]=4[CH2:5][CH2:4]3)=[N:23]2)[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1

Participants

4

Reactant 2

HCID 7516PhenylhydrazineHCID 54488542(1-Oxo-3,4-dihydronaphthalen-2(1H)-ylidene)acetic acid

Product 1

HCID 13712337HCID 13712337, compoundYield 20.6%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of 5 g of 1,2,3,4-tetrahydro-1-oxo-2-naphthylideneacetic acid and 3 g of phenylhydrazine in 100 ml of ethanol is refluxed for 10 hours. The precipitated crystals are collected by filtration, washed with ethanol and dissolved in 50 ml of acetic acid. The solution is refluxed under heating for 8 hours and the acetic acid is distilled off. The residue is extracted with ethyl acetate and the extract is washed with an aqueous sodium hydrogencarbonate solution. After drying over magnesium sulfate anhydride, the solvent is distilled off and to the residue is added ethanol. The precipitated crystals are collected by filtration and recrystallized from ethanol to give 1.4 g of 2-phenyl-5,6-dihydrobenzo[h]cinnolin-3(2H)-one as pale yellow needles, melting at 155°-157° C.

Workup

  1. temperatureis refluxed for 10 hours
  2. filtrationThe precipitated crystals are collected by filtration
  3. washwashed with ethanol
  4. dissolutiondissolved in 50 ml of acetic acid
  5. temperatureThe solution is refluxed
  6. temperatureunder heating for 8 hours
  7. distillationthe acetic acid is distilled off
  8. extractionThe residue is extracted with ethyl acetate
  9. washthe extract is washed with an aqueous sodium hydrogencarbonate solution
  10. dry with materialAfter drying over magnesium sulfate anhydride
  11. distillationthe solvent is distilled off and to the residue
  12. additionis added ethanol
  13. filtrationThe precipitated crystals are collected by filtration
  14. customrecrystallized from ethanol

Sources & evidence

ORD record
ord-854ed0dadd6548e791fd55a2adace05d
Source dataset
uspto-grants-1988_11
Patent number
US04782057

Reaction notes

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