Hydrazine hydrate (1:1) → 2-Hydrazinylpyridine-4-carbonitrile

HRID 1913171Notes

Reaction equation

HRID 1913171 reaction equation
Cl[C:2]1[CH:3]=[C:4]([CH:7]=[CH:8][N:9]=1)[C:5]#[N:6].O.[NH2:11][NH2:12]>C(O)CCC.C1COCC1>[NH:11]([C:2]1[CH:3]=[C:4]([CH:7]=[CH:8][N:9]=1)[C:5]#[N:6])[NH2:12]

Participants

5

Reactant 2

HCID 24654Hydrazine hydrate (1:1)HCID 5686382-Chloro-4-cyanopyridine

Product 1

HCID 201187142-Hydrazinylpyridine-4-carbonitrile

Reagents, catalysts & solvents 2

HCID 2631-ButanolSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
110 °C

Procedure

20.0 g (144 mmol) of 2-chloroisonicotinonitrile are initially charged in 150 ml of 1-butanol, 303 ml (303 mmol) of a 1 M solution of hydrazine hydrate in THF are added and the mixture is heated for 16 h (bath temperature 110° C.). The mixture is concentrated and the residue is purified by flash chromatography on silica gel (mobile phase: dichloromethane/methanol 10:1).

Workup

  1. concentrationThe mixture is concentrated
  2. customthe residue is purified by flash chromatography on silica gel (mobile phase: dichloromethane/methanol 10:1)

Sources & evidence

ORD record
ord-4b56da6c308746fb9d985a66ec02c867
Source dataset
uspto-grants-2013_12
Patent number
US08609698B2

Reaction notes

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