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

HRID 871702Notes

Reaction equation

HRID 871702 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-6fc1fe076531407fbfa20baae504bf4e
Source dataset
uspto-grants-2015_03
Patent number
US08969587B2

Reaction notes

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