Ethyl 5-hydrazino-3-(pyridin-4-yl)-1,2,4-triazine-6-carboxylate → Ethyl 3-(pyridin-4-yl)-1,2,4-triazin-6-carboxylate

HRID 352821Notes

Reaction equation

HRID 352821 reaction equation
N([C:3]1[N:4]=[C:5]([C:14]2[CH:19]=[CH:18][N:17]=[CH:16][CH:15]=2)[N:6]=[N:7][C:8]=1[C:9]([O:11][CH2:12][CH3:13])=[O:10])N>C(O)C.[Hg]=O>[N:17]1[CH:18]=[CH:19][C:14]([C:5]2[N:6]=[N:7][C:8]([C:9]([O:11][CH2:12][CH3:13])=[O:10])=[CH:3][N:4]=2)=[CH:15][CH:16]=1

Participants

4

Reactant 1

HCID 22709653Ethyl 5-hydrazino-3-(pyridin-4-yl)-1,2,4-triazine-6-carboxylate

Product 1

HCID 22711342Ethyl 3-(pyridin-4-yl)-1,2,4-triazin-6-carboxylateYield 52%

Reagents, catalysts & solvents 2

HCID 30856Mercuric oxideCatalystHCID 702EthanolSolvent

Procedure

In ethanol (5 ml) was suspended ethyl 5-hydrazino-3-(pyridin-4-yl)-1,2,4-triazine-6-carboxylate (50 mg). To the resulting suspension, mercury (II) oxide (98 mg) was added and the resulting mixture was heated under reflux for 9 hours. After completion of the reaction, the insoluble matter was removed through Celite filtration. The filtrate was concentrated and the concentrate was separated into layers by the addition of ethyl acetate and water. The organic layer thus obtained was dried over anhydrous magnesium sulfate. The filtrate was concentrated, whereby a crudely purified product of the title compound (23 mg, pale yellow powder) was obtained.

Workup

  1. temperaturethe resulting mixture was heated
  2. temperatureunder reflux for 9 hours
  3. customAfter completion of the reaction
  4. customthe insoluble matter was removed through Celite filtration
  5. concentrationThe filtrate was concentrated
  6. customthe concentrate was separated into layers by the addition of ethyl acetate and water
  7. customThe organic layer thus obtained
  8. dry with materialwas dried over anhydrous magnesium sulfate
  9. concentrationThe filtrate was concentrated

Sources & evidence

ORD record
ord-2854f45b84e748d596a35ef1814faa13
Source dataset
uspto-grants-2004_06
Patent number
US06747023B1

Reaction notes

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