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

HRID 982509Notes

Reaction equation

HRID 982509 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-dd7e4cb9a35d4c0faf38a7d9e86852a8
Source dataset
uspto-grants-1991_02
Patent number
US04996325

Reaction notes

Loading…