Chloroform → HCID 21537926, compound

HRID 1076693Notes

Reaction equation

HRID 1076693 reaction equation
[N:1]1[CH:6]=[CH:5][C:4]([CH:7]=[C:8]2[CH2:17][CH:16]([CH3:18])[C:15]3[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=3)[C:9]2=O)=[CH:3][CH:2]=1.[NH2:20][NH2:21].C(Cl)(Cl)Cl>C(O)C>[CH3:18][CH:16]1[C:15]2[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=2)[C:9]2=[N:20][NH:21][CH:7]([C:4]3[CH:5]=[CH:6][N:1]=[CH:2][CH:3]=3)[CH:8]2[CH2:17]1

Participants

5

Reactant 3

HCID 6212ChloroformHCID 9321HydrazineHCID 54142473HCID 54142473, compound

Product 1

HCID 21537926HCID 21537926, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a mixture of 25 grams of 2-(4-pyridylmethylene)-3,4-dihydro-4-methyl-1 (2H)-naphthalenone and 5 grams of hydrazine in 150 ml of ethanol is added sufficient chlorform to dissolve all the reactants. The solution is refluxed overnight under anhydrous conditions. After cooling, the reaction mixture is filtered and the solvent removed by evaporation to yield 5-methyl-3-(4-pyridyl)-3,3a,4,5-tetrahydro-2H-naphtho[1,2-c]Pyrazole. This is chromatographed on silica using benzene as the eluant to yield 4,5-dihydro-5-methyl-3l -(4-pyridyl)-2H-naphtho[1,2c]pyrazole.

Workup

  1. dissolutionto dissolve all the reactants
  2. temperatureThe solution is refluxed overnight under anhydrous conditions
  3. temperatureAfter cooling
  4. filtrationthe reaction mixture is filtered
  5. customthe solvent removed by evaporation

Sources & evidence

ORD record
ord-dce0de805b474754a8481953eeafa8d9
Source dataset
uspto-grants-1976_05
Patent number
US03957816

Reaction notes

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