3-Pyridinecarboxaldehyde → 4,5-Dihydro-6-methyl-4-((3-pyridinylmethylene)amino)-1,2,4-triazin-3(2H)-one

HRID 2106641Notes

Reaction equation

HRID 2106641 reaction equation
[N:1]1[CH:6]=[CH:5][CH:4]=[C:3]([CH:7]=O)[CH:2]=1.[O:9]=[C:10]1[N:15]([NH2:16])[CH2:14][C:13]([CH3:17])=[N:12][NH:11]1>Cl.C(O)C>[O:9]=[C:10]1[N:15]([N:16]=[CH:7][C:3]2[CH:2]=[N:1][CH:6]=[CH:5][CH:4]=2)[CH2:14][C:13]([CH3:17])=[N:12][NH:11]1

Participants

5

Reactant 2

HCID 103713-PyridinecarboxaldehydeHCID 109755004-Amino-6-methyl-2,5-dihydro-1,2,4-triazin-3-one

Product 1

HCID 863704,5-Dihydro-6-methyl-4-((3-pyridinylmethylene)amino)-1,2,4-triazin-3(2H)-one

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidCatalystHCID 702EthanolSolvent

Procedure

26.8 g (0.25 mole) of pyridine-3-carbaldehyde and 1 drop of concentrated HCl are added at 60° C. to 32 g (0.25 mole) of 2,3,4,5-tetrahydro-3-oxo-4-amino-6-methyl-1,2,4-triazine dissolved in 250 ml of ethanol. After boiling for half an hour under reflux, the reaction mixture is cooled and the solid portion is isolated by filtration, washed with ether and dried to give the title compound of formula ##STR22## in the form of a colourless solid; m.p. 227°-228° C.; yield: 48 g (90%).

Workup

  1. waitAfter boiling for half an hour
  2. temperatureunder reflux
  3. temperaturethe reaction mixture is cooled
  4. customthe solid portion is isolated by filtration
  5. washwashed with ether
  6. customdried

Sources & evidence

ORD record
ord-051100895ca942cea5efa5ccfa6b894f
Source dataset
uspto-grants-1990_06
Patent number
US04931439

Reaction notes

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