Hydrazine hydrate (1:1) → 3-(propan-2-yl)-1H-pyrazol-5-amine

HRID 1485292Notes

Reaction equation

HRID 1485292 reaction equation
[CH3:1][CH:2]([CH3:8])[C:3](=O)[CH2:4][C:5]#[N:6].O.[NH2:10][NH2:11]>CCO.CCOC(C)=O>[CH:2]([C:3]1[NH:11][N:10]=[C:5]([NH2:6])[CH:4]=1)([CH3:8])[CH3:1]

Participants

5

Reactant 2

HCID 24654Hydrazine hydrate (1:1)HCID 101299214-Methyl-3-oxopentanenitrile

Product 1

HCID 27695273-(propan-2-yl)-1H-pyrazol-5-amineYield 59.2%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 4-methyl-3-oxopentanenitrile (15 g, 135 mmol) in EtOH (150 mL) was added hydrazine hydrate (7.30 g, 146 mmol) slowly at 0° C. The reaction mixture was heated to reflux for 4 h. Removal of EtOH under reduced pressure gave an oily residue that was dissolved in EtOAc (200 mL) and washed with freshly prepared brine (2×50 mL). The organic layer was dried over anhydrous sodium sulfate. Removal of EtOAc gave 5-isopropyl-1H-pyrazol-3-amine, Compound (ii) (10 g, 59% yield). 1H NMR (400 MHz, CDCl3) δ (ppm): 1.22 (d, 6H), 2.80-2.92 (m, 1H), 4.80 (brs, 3H), 5.41 (s, 1H).

Workup

  1. temperatureThe reaction mixture was heated
  2. temperatureto reflux for 4 h
  3. customRemoval of EtOH under reduced pressure
  4. customgave an oily residue that
  5. washwashed with freshly prepared brine (2×50 mL)
  6. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  7. customRemoval of EtOAc

Sources & evidence

ORD record
ord-05a5198731fc48fdbf61b7d338a42fc2
Source dataset
uspto-grants-2016_08
Patent number
US09422267B2

Reaction notes

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