Hydrazine → 4-Hydrazinylpyridin-2(1H)-one

HRID 631653Notes

Reaction equation

HRID 631653 reaction equation
[NH2:1][NH2:2].O[C:4]1[C:5]([OH:10])=[N:6][CH:7]=[CH:8][CH:9]=1>COCCOC>[NH:1]([C:9]1[CH:8]=[CH:7][NH:6][C:5](=[O:10])[CH:4]=1)[NH2:2]

Participants

4

Reactant 2

HCID 9321HydrazineHCID 178516237HCID 178516237, compound

Product 1

HCID 136108294-Hydrazinylpyridin-2(1H)-oneYield 78%

Reagents, catalysts & solvents 1

HCID 80711,2-DimethoxyethaneSolvent

Procedure

To a solution of hydrazine (8 mL) in DME (40 mL) was added dihydroxypyridine (2.00 g, 18 mmol) and the reaction heated at reflux overnight. The solution was cooled to rt, and the solids removed by filtration. The filtrate was concentrated and the resulting solid crystallized from hot EtOH to afford 4-hydrazinylpyridin-2(1H)-one (1.75 g, 78% yield). LC-MS (ESI) m/z 126 (M+H)+.

Workup

  1. temperaturethe reaction heated
  2. temperatureat reflux overnight
  3. customthe solids removed by filtration
  4. concentrationThe filtrate was concentrated
  5. customthe resulting solid crystallized from hot EtOH

Sources & evidence

ORD record
ord-7237a71d73034ee9ab2ff86d01f650e4
Source dataset
uspto-grants-2016_04
Patent number
US09320739B2

Reaction notes

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