Phenylhydrazine → 4-(1-Phenyl-1H-1,2,4-triazol-5-yl)pyridine

HRID 128454

Reaction equation

HRID 128454 reaction equation
[C:1]1([NH:7][NH2:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.CN([CH:12]=[N:13][C:14](=O)[C:15]1[CH:20]=[CH:19][N:18]=[CH:17][CH:16]=1)C>C(O)(=O)C>[C:1]1([N:7]2[C:14]([C:15]3[CH:20]=[CH:19][N:18]=[CH:17][CH:16]=3)=[N:13][CH:12]=[N:8]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

4

Reactant 2

HCID 7516PhenylhydrazineHCID 12569643N-Dimethylaminomethylene-isonicotinamide

Product 1

HCID 128502974-(1-Phenyl-1H-1,2,4-triazol-5-yl)pyridine

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Conditions

Temperature
90 °C

Procedure

To a solution of 6.9 g. of phenylhydrazine in 100 ml. of acetic acid is added 10.0 g. of N-(dimethylaminomethylene)isonicotinamide. The reaction mixture is stirred at 90° C. for 1.5 hours and then evaporated in vacuo to an orange oil. This oil is dissolved in 250 ml. of chloroform, washed with 60 ml. of saturated sodium bicarbonate solution, then with 60 ml. of water, dried over sodium sulfate and filtered. The chloroform is removed and the residue is dissolved in 60 ml. of ether. Cooling produces 8.8 g. of the desired product as tan crystals, mp. 92°-94° C.

Workup

  1. customevaporated in vacuo to an orange oil
  2. dissolutionThis oil is dissolved in 250 ml
  3. washof chloroform, washed with 60 ml
  4. dry with materialof water, dried over sodium sulfate
  5. filtrationfiltered
  6. customThe chloroform is removed
  7. dissolutionthe residue is dissolved in 60 ml
  8. temperatureCooling
  9. customproduces 8.8 g

Sources & evidence

ORD record
ord-0a98110ee36f40d5b1f1c8b0c4729bee
Source dataset
uspto-grants-1981_03
Patent number
US04259504

Linked notes

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