Hydrazine hydrate (1:1) → 6-Hydrazinylnicotinonitrile

HRID 1913182Notes

Reaction equation

HRID 1913182 reaction equation
O.[NH2:2][NH2:3].Cl[C:5]1[CH:12]=[CH:11][C:8]([C:9]#[N:10])=[CH:7][N:6]=1>O>[NH:2]([C:5]1[N:6]=[CH:7][C:8]([C:9]#[N:10])=[CH:11][CH:12]=1)[NH2:3]

Participants

4

Reactant 2

HCID 24654Hydrazine hydrate (1:1)HCID 51520946-Chloro-3-pyridinecarbonitrile

Product 1

HCID 5841956-Hydrazinylnicotinonitrile

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
100 °C

Procedure

90.3 g (1.8 mol) of hydrazine hydrate are added to 25.0 g (180.4 mmol) of 6-chloronicotinonitrile, and the mixture is stirred at a bath temperature of 100° C. for 15 min. The reaction mixture is cooled to RT, diluted with water and stirred at RT for 30 min. The precipitate formed is filtered off, the filter residue is washed with water and the crystals are air-dried for 24 h and recrystallized once from ethyl acetate.

Workup

  1. temperatureThe reaction mixture is cooled to RT
  2. stirringstirred at RT for 30 min
  3. customThe precipitate formed
  4. filtrationis filtered off
  5. washthe filter residue is washed with water
  6. customthe crystals are air-dried for 24 h
  7. customrecrystallized once from ethyl acetate

Sources & evidence

ORD record
ord-22aaab2991d04eaeaeb3f1333e4e296d
Source dataset
uspto-grants-2013_12
Patent number
US08609698B2

Reaction notes

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