Sodium Hydroxide → 1-(tetrahydro-2H-pyran-4-yl)-1H-pyrazol-5-amine

HRID 1521733Notes

Reaction equation

HRID 1521733 reaction equation
[O:1]1[CH2:6][CH2:5][C:4](=[N:7][NH:8][CH2:9][CH2:10][C:11]#[N:12])[CH2:3][CH2:2]1.[OH-].[Na+]>C(O)CC>[O:1]1[CH2:2][CH2:3][CH:4]([N:7]2[C:11]([NH2:12])=[CH:10][CH:9]=[N:8]2)[CH2:5][CH2:6]1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 672357923-[2-(Tetrahydro-4H-pyran-4-ylidene)hydrazinyl]propanenitrile

Product 1

HCID 436086621-(tetrahydro-2H-pyran-4-yl)-1H-pyrazol-5-amineYield 32%

Reagents, catalysts & solvents 1

HCID 10311-PropanolSolvent

Procedure

To a solution of 3-[2-(tetrahydro-4H-pyran-4-ylidene)hydrazinyl]propanenitrile (5 g, 30 mmol) in 1-propanol (50 mL) is added NaOH (29 mg, 0.74 mmol) and reaction mixture is heated at reflux for 16 h. The solvent is evaporated under reduced pressure and the residue is filtered through neutral alumina eluting with ethyl acetate to afford the title compound as a yellow solid (1.6 g, 32%) which is used in the next step without purification.

Workup

  1. temperatureis heated
  2. temperatureat reflux for 16 h
  3. customThe solvent is evaporated under reduced pressure
  4. filtrationthe residue is filtered through neutral alumina eluting with ethyl acetate

Sources & evidence

ORD record
ord-401b8e2a09f24a19b2b3a396ae29e546
Source dataset
uspto-grants-2015_07
Patent number
US09073926B2

Reaction notes

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