Hydrochloric Acid → 2-(5-amino-3-tert-butyl-1H-pyrazol-1-yl)ethan-1-ol

HRID 75581

Reaction equation

HRID 75581 reaction equation
[CH3:1][C:2]([CH3:9])([CH3:8])[C:3](=O)[CH2:4][C:5]#[N:6].Cl.[NH:11]([CH2:13][CH2:14][OH:15])[NH2:12]>C(O)C>[NH2:6][C:5]1[N:11]([CH2:13][CH2:14][OH:15])[N:12]=[C:3]([C:2]([CH3:9])([CH3:8])[CH3:1])[CH:4]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 80172-HydrazinoethanolHCID 108871Pentanenitrile, 4,4-dimethyl-3-oxo-

Product 1

HCID 162278772-(5-amino-3-tert-butyl-1H-pyrazol-1-yl)ethan-1-olYield 97.3%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution of 4,4-dimethyl-3-oxo-pentanenitrile (5.00 g, 40.0 mmol), concentrated HCl (0.1 mL), and 2-hydrazino ethanol (2.98 mL, 44.0 mmol) in ethanol (40 mL) was refluxed for 20 h. The reaction mixture was then concentrated in vacuo. The resulting oily solid was washed with cyclohexane (30 mL), and dissolved in MeOH (5 mL) and H2O (5 mL) and lyophilised to give the title compound as a white powder (7.13 g, 97%). LCMS (Method 3): Rt 0.43 min, m/z 184 [MH+].

Workup

  1. concentrationThe reaction mixture was then concentrated in vacuo
  2. washThe resulting oily solid was washed with cyclohexane (30 mL)
  3. dissolutiondissolved in MeOH (5 mL)

Sources & evidence

ORD record
ord-2de6a3d9b2ca4b78bda6fb2329a4e94d
Source dataset
uspto-grants-2014_09
Patent number
US08835431B2

Linked notes

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