Water → 3-(4-pyridyl)-1,2,4-triazine

HRID 1635599Notes

Reaction equation

HRID 1635599 reaction equation
O.[C:2]([C:4]1[CH:9]=[CH:8][N:7]=[CH:6][CH:5]=1)#[N:3].O.[NH2:11][NH2:12].[C:13]1([CH3:19])C=CC=CC=1>>[N:7]1[CH:8]=[CH:9][C:4]([C:2]2[N:11]=[N:12][CH:13]=[CH:19][N:3]=2)=[CH:5][CH:6]=1

Participants

5

Reactant 4

HCID 962WaterHCID 1140TolueneHCID 75064-CyanopyridineHCID 24654Hydrazine hydrate (1:1)

Product 1

HCID 114125253-(4-pyridyl)-1,2,4-triazineYield 85.2%

Conditions

Temperature
50 °C

Procedure

In a 2000-ml four-necked flask were charged 200 ml of water, 200.0 g (1.92 mole) of 4-cyanopyridine and 192.0 g (3.84 mole) of hydrazine monohydrate. The mixture was reacted for 4 hours under stirring at 50° C. After confirmation of the disappearance of the raw material by HPLC analysis, 400 ml of toluene was added and excessive hydrazine monohydrate was distilled off. This operation was conducted again. To the residue were successively added 800 ml of water and 278.4 g (1.92 mole) of a 40% aqueous glyoxal solution. The mixture was reacted for 2 hours at an external temperature of 100° C. After completion of the reaction, the reaction mixture was cooled to 5° C., whereby 222.4 g (yield: 85.2%) of the target compound was obtained as pale yellow crystals.

Workup

  1. customThe mixture was reacted for 4 hours
  2. distillationexcessive hydrazine monohydrate was distilled off
  3. customThe mixture was reacted for 2 hours at an external temperature of 100° C
  4. customAfter completion of the reaction
  5. temperaturethe reaction mixture was cooled to 5° C.

Sources & evidence

ORD record
ord-bd2533a30b04444889c2ad80cbdc40fe
Source dataset
uspto-grants-2003_01
Patent number
US06509469B1

Reaction notes

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