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

HRID 264764Notes

Reaction equation

HRID 264764 reaction equation
Cl.[NH2:2][N:3]1[CH2:8][C:7]([CH3:9])=[N:6][NH:5][C:4]1=[O:10].[OH-].[Na+].[N:13]1[CH:18]=[CH:17][CH:16]=[C:15]([CH:19]=O)[CH:14]=1>CO.O>[CH3:9][C:7]1[CH2:8][N:3]([N:2]=[CH:19][C:15]2[CH:14]=[N:13][CH:18]=[CH:17][CH:16]=2)[C:4](=[O:10])[NH:5][N:6]=1

Participants

6

Reactant 3

HCID 103713-PyridinecarboxaldehydeHCID 14798Sodium HydroxideHCID 190369254-Amino-6-methyl-4,5-dihydro-1,2,4-triazin-3(2H)-one--hydrogen chloride (1/1)

Product 1

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

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Conditions

Temperature
5 °C

Procedure

To a suspension of 164 g of 4-amino-6-methyl-3-oxo-2,3,4,5-tetrahydro-1,2,4-triazine hydrochloride in 500 ml methanol a 50% NaOH solution is added until a pH of 6 is reached. Now 486 g of a solution containing 22% 3-pyridinaldehyde in water is added maintaining a temperature below 70° C. After the addition is completed the reaction mixture is kept at 65° C. for two hours. Then the suspension is cooled to about 5° C., filtered and dried to yield the title compound.

Workup

  1. additionis added until a pH of 6
  2. additionis added
  3. temperaturemaintaining a temperature below 70° C
  4. additionAfter the addition
  5. filtrationfiltered
  6. customdried

Sources & evidence

ORD record
ord-40668812f96c4472b37018ff072a65ca
Source dataset
uspto-grants-1997_07
Patent number
US05646288

Reaction notes

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