Propionitrile → 3-[2-(Tetrahydro-4H-pyran-4-ylidene)hydrazinyl]propanenitrile

HRID 1521732Notes

Reaction equation

HRID 1521732 reaction equation
[C:1](#[N:4])[CH2:2][CH3:3].[OH2:5].[NH2:6][NH2:7].O1[CH2:13][CH2:12][C:11](=O)[CH2:10][CH2:9]1>C(O)C>[O:5]1[CH2:13][CH2:12][C:11](=[N:6][NH:7][CH2:3][CH2:2][C:1]#[N:4])[CH2:10][CH2:9]1

Participants

5

Reactant 3

HCID 7854PropionitrileHCID 24654Hydrazine hydrate (1:1)HCID 121599Tetrahydro-4H-pyran-4-one

Product 1

HCID 672357923-[2-(Tetrahydro-4H-pyran-4-ylidene)hydrazinyl]propanenitrile

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution of propanenitrile (5 g, 94 mmol) in ethanol at 0° C. is added hydrazine hydrate (4.6 g, 91 mmol), dropwise. The reaction mixture is stirred at ambient temperature for 16 h after. The mixture is cooled to 0° C. and tetrahydropyran-4-one (9 g, 90 mmol) is added slowly. The reaction continues to stir at ambient temperature for an additional 5 h. The solvent is evaporated under reduced pressure to afford the title compound as a highly viscous liquid (15 g, >99%) which is used in the next step without purification.

Workup

  1. temperatureThe mixture is cooled to 0° C.
  2. stirringto stir at ambient temperature for an additional 5 h
  3. customThe solvent is evaporated under reduced pressure

Sources & evidence

ORD record
ord-5e5265d224064545bd242ec0174044e1
Source dataset
uspto-grants-2015_07
Patent number
US09073926B2

Reaction notes

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