Tetrahydrofuran → 2-Hydrazinylpyridine-4-carbonitrile

HRID 514325Notes

Reaction equation

HRID 514325 reaction equation
Cl[C:2]1[CH:7]=[C:6]([C:8]#[N:9])[CH:5]=[CH:4][N:3]=1.O.[NH2:11][NH2:12].C1COCC1>C(O)CCC>[NH:11]([C:2]1[CH:7]=[C:6]([C:8]#[N:9])[CH:5]=[CH:4][N:3]=1)[NH2:12]

Participants

5

Reactant 3

HCID 8028TetrahydrofuranHCID 24654Hydrazine hydrate (1:1)HCID 5686382-Chloro-4-cyanopyridine

Product 1

HCID 201187142-Hydrazinylpyridine-4-carbonitrileYield 18%

Reagents, catalysts & solvents 1

HCID 2631-ButanolSolvent

Conditions

Temperature
60 °C

Procedure

To a solution of 2-chloropyridine-4-carbonitrile (20.0 g, 144 mmol) in 1-butanol (150 mL) was added 1 M solution of hydrazine hydrate in THF (303 mL, 303 mmol) dropwise at rt. It was then heated at 60° C. overnight. The mixture was concentrated, and the residue was purified by flash column chromatography (CH2Cl2/MeOH=20/1) to afford the title compound (3.5 g, 18%) as a white solid. [M+H] Calc'd for C6H6N4, 135. Found, 135.

Workup

  1. concentrationThe mixture was concentrated
  2. customthe residue was purified by flash column chromatography (CH2Cl2/MeOH=20/1)

Sources & evidence

ORD record
ord-26ee47ec087e4b198265ccbb98f6a1de
Source dataset
uspto-grants-2015_08
Patent number
US09107916B2

Reaction notes

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